Is it worth paying tax via credit card?

[Anonymous]

Anonymous wrote:

Anonymous wrote:
DH and I are staying at the Park Hyatt Tokyo in June for 7 nights using 315K points plus a Suite Upgrade Certificate. This is peak pricing! The cash price for the most entry level room over the same dates is $14K. When you factor in the suite upgrade, we’re looking at a standard suite that would otherwise cost $22K.

That's a great use of points. I'm surprsied Hyatt Grand Tokyo is so cheap -- even now I see it's coming up at 40k/night for those dates. I know it just reopened after a recent renovation -- enjoy!

[Anonymous]

Anonymous wrote:

Anonymous wrote:No, you have to pay a 3% fee. That would be almost $4000 for me this year and my credit limit isn't that high anyway.

OP, unlike this moron, we follow IRS suggestions and use Pay1040 to make periodic tax payments at a very reasonable rate of 1.75%. We use our Chase Freedom Unlimited card (which has a $75K limit) to make estimated quarterly payments of around $53K each. This works out to be about $3710 in fees. The spending earns us 1.5X per dollar spent which is about 318K Chase points per year. We also have a CSR credit card which allows us to transfer 1:1 to Hyatt points which are nominally valued at about 1.7¢ each. This means we’re getting at least $5406 in value for only a $3710 expense.

Truthfully, though, we cash in those 318K Hyatt points to book multiple rooms or suites for week-long vacations at places like the Park Hyatt Maldives, Alila Ventana Big Sur, or the Impressions by Secrets in Cancun.

DH and I are staying at the Park Hyatt Tokyo in June for 7 nights using 315K points plus a Suite Upgrade Certificate. This is peak pricing! The cash price for the most entry level room over the same dates is $14K. When you factor in the suite upgrade, we’re looking at a standard suite that would otherwise cost $22K.

So, yeah, we’re cool spending an extra $4K in CC fees to land a luxury suite in Tokyo that would cost a cash-paying customer an extra $18K. This is why our family takes 5-6 luxury vacations every year to most people’s 1-2.

My kids have activities and we can only travel Christmas and spring break. When I looked to use points at a JW Marriott for Christmas, it was 100,000 a night per room. So your 300,000 points would have bought me 3 nights. Big deal. Not worth my time. My credit card limit isn’t big enough for the $200k to the feds I paid the other day. I wish we could travel at off peak cheap times. Maybe in a few years.

[Anonymous]

We had to for MD because it was not allowing us to do an electronic transfer and it was 10pm on the 15. The 2.5 or whatever fee hurts but at least we get some miles out of it.

[Anonymous]

Anonymous wrote:Is it worth the trouble paying your tax due with a credit card, for the points or whatever? Also, is it really secure, because you have to leave the e-file process, pay with the card, then come back to the e-file process? I'm not looking for new problems even though many people probably do it with the card.

It could be Ask chatgpt for the math.

[Anonymous]

Anonymous wrote:

Anonymous wrote:No, you have to pay a 3% fee. That would be almost $4000 for me this year and my credit limit isn't that high anyway.

OP, unlike this moron, we follow IRS suggestions and use Pay1040 to make periodic tax payments at a very reasonable rate of 1.75%. We use our Chase Freedom Unlimited card (which has a $75K limit) to make estimated quarterly payments of around $53K each. This works out to be about $3710 in fees. The spending earns us 1.5X per dollar spent which is about 318K Chase points per year. We also have a CSR credit card which allows us to transfer 1:1 to Hyatt points which are nominally valued at about 1.7¢ each. This means we’re getting at least $5406 in value for only a $3710 expense.

Truthfully, though, we cash in those 318K Hyatt points to book multiple rooms or suites for week-long vacations at places like the Park Hyatt Maldives, Alila Ventana Big Sur, or the Impressions by Secrets in Cancun.

DH and I are staying at the Park Hyatt Tokyo in June for 7 nights using 315K points plus a Suite Upgrade Certificate. This is peak pricing! The cash price for the most entry level room over the same dates is $14K. When you factor in the suite upgrade, we’re looking at a standard suite that would otherwise cost $22K.

So, yeah, we’re cool spending an extra $4K in CC fees to land a luxury suite in Tokyo that would cost a cash-paying customer an extra $18K. This is why our family takes 5-6 luxury vacations every year to most people’s 1-2.

I love this. I assume you are a business owner. When you have enough income to stash a bunch of points feed a good move.

[Anonymous]

Anonymous wrote:

Anonymous wrote:No, you have to pay a 3% fee. That would be almost $4000 for me this year and my credit limit isn't that high anyway.

OP, unlike this moron, we follow IRS suggestions and use Pay1040 to make periodic tax payments at a very reasonable rate of 1.75%. We use our Chase Freedom Unlimited card (which has a $75K limit) to make estimated quarterly payments of around $53K each. This works out to be about $3710 in fees. The spending earns us 1.5X per dollar spent which is about 318K Chase points per year. We also have a CSR credit card which allows us to transfer 1:1 to Hyatt points which are nominally valued at about 1.7¢ each. This means we’re getting at least $5406 in value for only a $3710 expense.

Truthfully, though, we cash in those 318K Hyatt points to book multiple rooms or suites for week-long vacations at places like the Park Hyatt Maldives, Alila Ventana Big Sur, or the Impressions by Secrets in Cancun.

DH and I are staying at the Park Hyatt Tokyo in June for 7 nights using 315K points plus a Suite Upgrade Certificate. This is peak pricing! The cash price for the most entry level room over the same dates is $14K. When you factor in the suite upgrade, we’re looking at a standard suite that would otherwise cost $22K.

So, yeah, we’re cool spending an extra $4K in CC fees to land a luxury suite in Tokyo that would cost a cash-paying customer an extra $18K. This is why our family takes 5-6 luxury vacations every year to most people’s 1-2.

We do this too with about the same tax burden but I definitely don’t have time for 5-6 vacations a year with the amount I have to work to have this much of a tax burden. More like 1-2 vacays!

There was no need to call the PP a moron.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:No, you have to pay a 3% fee. That would be almost $4000 for me this year and my credit limit isn't that high anyway.

OP, unlike this moron, we follow IRS suggestions and use Pay1040 to make periodic tax payments at a very reasonable rate of 1.75%. We use our Chase Freedom Unlimited card (which has a $75K limit) to make estimated quarterly payments of around $53K each. This works out to be about $3710 in fees. The spending earns us 1.5X per dollar spent which is about 318K Chase points per year. We also have a CSR credit card which allows us to transfer 1:1 to Hyatt points which are nominally valued at about 1.7¢ each. This means we’re getting at least $5406 in value for only a $3710 expense.

Truthfully, though, we cash in those 318K Hyatt points to book multiple rooms or suites for week-long vacations at places like the Park Hyatt Maldives, Alila Ventana Big Sur, or the Impressions by Secrets in Cancun.

DH and I are staying at the Park Hyatt Tokyo in June for 7 nights using 315K points plus a Suite Upgrade Certificate. This is peak pricing! The cash price for the most entry level room over the same dates is $14K. When you factor in the suite upgrade, we’re looking at a standard suite that would otherwise cost $22K.

So, yeah, we’re cool spending an extra $4K in CC fees to land a luxury suite in Tokyo that would cost a cash-paying customer an extra $18K. This is why our family takes 5-6 luxury vacations every year to most people’s 1-2.

I love this. I assume you are a business owner. When you have enough income to stash a bunch of points feed a good move.

No. We are not small business owners. The $53K we pay in quarterly estimated taxes was in anticipation of dividends, interest, and capital gains in our taxable brokerage accounts. In 2025, these passive sources constituted $710K of our HHI, which was $2.8M total.

To the point of the original post, we put way more than just $212K per year on credit cards. That’s just one piece of the puzzle that is specific to income taxes. We actually put close to $100K per month in expenses on our credit cards – mostly travel credit cards and most expenses with no fees.

DH and I both work full time, we both travel 2-3 times per month (1-2 times together), our kids are in college, and we both earn a ton of miles and points through paid business travel. The CC points are the icing on the cake. This is all easy stuff to figure out. However, every time we travel we’re blown away by people who humblebrag about their extreme wealth (e.g., like the $1300/hour snatch) but then can’t seem to navigate the points and miles game to travel frequently, luxuriously, and comfortably with minimal friction or out of pocket expense. These are the losers that are so rich (aka so stupid) that they can afford to waste money, make strategic spending blunders, and operate with extreme inefficiency.

No thanks. DH and I operate at a higher level.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:No, you have to pay a 3% fee. That would be almost $4000 for me this year and my credit limit isn't that high anyway.

OP, unlike this moron, we follow IRS suggestions and use Pay1040 to make periodic tax payments at a very reasonable rate of 1.75%. We use our Chase Freedom Unlimited card (which has a $75K limit) to make estimated quarterly payments of around $53K each. This works out to be about $3710 in fees. The spending earns us 1.5X per dollar spent which is about 318K Chase points per year. We also have a CSR credit card which allows us to transfer 1:1 to Hyatt points which are nominally valued at about 1.7¢ each. This means we’re getting at least $5406 in value for only a $3710 expense.

Truthfully, though, we cash in those 318K Hyatt points to book multiple rooms or suites for week-long vacations at places like the Park Hyatt Maldives, Alila Ventana Big Sur, or the Impressions by Secrets in Cancun.

DH and I are staying at the Park Hyatt Tokyo in June for 7 nights using 315K points plus a Suite Upgrade Certificate. This is peak pricing! The cash price for the most entry level room over the same dates is $14K. When you factor in the suite upgrade, we’re looking at a standard suite that would otherwise cost $22K.

So, yeah, we’re cool spending an extra $4K in CC fees to land a luxury suite in Tokyo that would cost a cash-paying customer an extra $18K. This is why our family takes 5-6 luxury vacations every year to most people’s 1-2.

I love this. I assume you are a business owner. When you have enough income to stash a bunch of points feed a good move.

No. We are not small business owners. The $53K we pay in quarterly estimated taxes was in anticipation of dividends, interest, and capital gains in our taxable brokerage accounts. In 2025, these passive sources constituted $710K of our HHI, which was $2.8M total.

To the point of the original post, we put way more than just $212K per year on credit cards. That’s just one piece of the puzzle that is specific to income taxes. We actually put close to $100K per month in expenses on our credit cards – mostly travel credit cards and most expenses with no fees.

DH and I both work full time, we both travel 2-3 times per month (1-2 times together), our kids are in college, and we both earn a ton of miles and points through paid business travel. The CC points are the icing on the cake. This is all easy stuff to figure out. However, every time we travel we’re blown away by people who humblebrag about their extreme wealth (e.g., like the $1300/hour snatch) but then can’t seem to navigate the points and miles game to travel frequently, luxuriously, and comfortably with minimal friction or out of pocket expense. These are the losers that are so rich (aka so stupid) that they can afford to waste money, make strategic spending blunders, and operate with extreme inefficiency.

No thanks. DH and I operate at a higher level.

You guys are insufferable. Yep, you are so smart with your credit card points nonsense, fancy hotels, and full time jobs LMAO

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:No, you have to pay a 3% fee. That would be almost $4000 for me this year and my credit limit isn't that high anyway.

OP, unlike this moron, we follow IRS suggestions and use Pay1040 to make periodic tax payments at a very reasonable rate of 1.75%. We use our Chase Freedom Unlimited card (which has a $75K limit) to make estimated quarterly payments of around $53K each. This works out to be about $3710 in fees. The spending earns us 1.5X per dollar spent which is about 318K Chase points per year. We also have a CSR credit card which allows us to transfer 1:1 to Hyatt points which are nominally valued at about 1.7¢ each. This means we’re getting at least $5406 in value for only a $3710 expense.

Truthfully, though, we cash in those 318K Hyatt points to book multiple rooms or suites for week-long vacations at places like the Park Hyatt Maldives, Alila Ventana Big Sur, or the Impressions by Secrets in Cancun.

DH and I are staying at the Park Hyatt Tokyo in June for 7 nights using 315K points plus a Suite Upgrade Certificate. This is peak pricing! The cash price for the most entry level room over the same dates is $14K. When you factor in the suite upgrade, we’re looking at a standard suite that would otherwise cost $22K.

So, yeah, we’re cool spending an extra $4K in CC fees to land a luxury suite in Tokyo that would cost a cash-paying customer an extra $18K. This is why our family takes 5-6 luxury vacations every year to most people’s 1-2.

I love this. I assume you are a business owner. When you have enough income to stash a bunch of points feed a good move.

No. We are not small business owners. The $53K we pay in quarterly estimated taxes was in anticipation of dividends, interest, and capital gains in our taxable brokerage accounts. In 2025, these passive sources constituted $710K of our HHI, which was $2.8M total.

To the point of the original post, we put way more than just $212K per year on credit cards. That’s just one piece of the puzzle that is specific to income taxes. We actually put close to $100K per month in expenses on our credit cards – mostly travel credit cards and most expenses with no fees.

DH and I both work full time, we both travel 2-3 times per month (1-2 times together), our kids are in college, and we both earn a ton of miles and points through paid business travel. The CC points are the icing on the cake. This is all easy stuff to figure out. However, every time we travel we’re blown away by people who humblebrag about their extreme wealth (e.g., like the $1300/hour snatch) but then can’t seem to navigate the points and miles game to travel frequently, luxuriously, and comfortably with minimal friction or out of pocket expense. These are the losers that are so rich (aka so stupid) that they can afford to waste money, make strategic spending blunders, and operate with extreme inefficiency.

No thanks. DH and I operate at a higher level.

Operating at a higher level!!!

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:No, you have to pay a 3% fee. That would be almost $4000 for me this year and my credit limit isn't that high anyway.

OP, unlike this moron, we follow IRS suggestions and use Pay1040 to make periodic tax payments at a very reasonable rate of 1.75%. We use our Chase Freedom Unlimited card (which has a $75K limit) to make estimated quarterly payments of around $53K each. This works out to be about $3710 in fees. The spending earns us 1.5X per dollar spent which is about 318K Chase points per year. We also have a CSR credit card which allows us to transfer 1:1 to Hyatt points which are nominally valued at about 1.7¢ each. This means we’re getting at least $5406 in value for only a $3710 expense.

Truthfully, though, we cash in those 318K Hyatt points to book multiple rooms or suites for week-long vacations at places like the Park Hyatt Maldives, Alila Ventana Big Sur, or the Impressions by Secrets in Cancun.

DH and I are staying at the Park Hyatt Tokyo in June for 7 nights using 315K points plus a Suite Upgrade Certificate. This is peak pricing! The cash price for the most entry level room over the same dates is $14K. When you factor in the suite upgrade, we’re looking at a standard suite that would otherwise cost $22K.

So, yeah, we’re cool spending an extra $4K in CC fees to land a luxury suite in Tokyo that would cost a cash-paying customer an extra $18K. This is why our family takes 5-6 luxury vacations every year to most people’s 1-2.

I love this. I assume you are a business owner. When you have enough income to stash a bunch of points feed a good move.

No. We are not small business owners. The $53K we pay in quarterly estimated taxes was in anticipation of dividends, interest, and capital gains in our taxable brokerage accounts. In 2025, these passive sources constituted $710K of our HHI, which was $2.8M total.

To the point of the original post, we put way more than just $212K per year on credit cards. That’s just one piece of the puzzle that is specific to income taxes. We actually put close to $100K per month in expenses on our credit cards – mostly travel credit cards and most expenses with no fees.

DH and I both work full time, we both travel 2-3 times per month (1-2 times together), our kids are in college, and we both earn a ton of miles and points through paid business travel. The CC points are the icing on the cake. This is all easy stuff to figure out. However, every time we travel we’re blown away by people who humblebrag about their extreme wealth (e.g., like the $1300/hour snatch) but then can’t seem to navigate the points and miles game to travel frequently, luxuriously, and comfortably with minimal friction or out of pocket expense. These are the losers that are so rich (aka so stupid) that they can afford to waste money, make strategic spending blunders, and operate with extreme inefficiency.

No thanks. DH and I operate at a higher level.

Operating at a higher level!!!

Exactly! Operating at a higher level of arrogance and unjustified smugness. PP’s DH probably pulls in $2.0M in earned income and $0.71M in investment income while the smug PP is raking in the remaining $90K per year working some go-nowhere, entirely remote, low-level position.

Probably was encouraged to start working again now that her kids are in college b/c her DH was tired of watching her lounge around the house, sipping on glasses of $1000/bottle wine, and passing out drunk every afternoon.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:The humblebragging on this thread is too funny.

Only one idiot taking 6 vacations

Actually, we travel for leisure at least once a month – only 5-6 of these trips are long enough (4+ nights) to be considered luxury vacations (e.g, this year it is Bali, Singapore, London, Tokyo, Maui, and Prague). Our shorter 2-3 night getaways are always via direct flights over long weekends (e.g., this year it is Punta Cana, NYC, Las Vegas, Turks & Caicos, New Orleans, Mexico City, Napa Valley, and Lisbon).

Or I guess we could just stay at home, pay all our bills with bank transfers, ignore the wonders of CC benefits and travel, clip coupons, and sip on glasses of boxed wine while endlessly watching YouTube videos like all the other DCUMs. Oh but we could spice it up with an occasional splurge on an overnight to Rehoboth Beach or maybe even the Greenbrier. Pathetic.

you really are not nearly as clever as you think you are

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:The humblebragging on this thread is too funny.

Only one idiot taking 6 vacations

Actually, we travel for leisure at least once a month – only 5-6 of these trips are long enough (4+ nights) to be considered luxury vacations (e.g, this year it is Bali, Singapore, London, Tokyo, Maui, and Prague). Our shorter 2-3 night getaways are always via direct flights over long weekends (e.g., this year it is Punta Cana, NYC, Las Vegas, Turks & Caicos, New Orleans, Mexico City, Napa Valley, and Lisbon).

Or I guess we could just stay at home, pay all our bills with bank transfers, ignore the wonders of CC benefits and travel, clip coupons, and sip on glasses of boxed wine while endlessly watching YouTube videos like all the other DCUMs. Oh but we could spice it up with an occasional splurge on an overnight to Rehoboth Beach or maybe even the Greenbrier. Pathetic.

you really are not nearly as clever as you think you are

Jealous much?