Anonymous
Post 04/15/2026 10:53     Subject: Is it worth paying tax via credit card?
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.

I am intrigued. How much do you spend on CCs a year? Do you just use the chase freedom card? How do you keep up with converting points etc?
Anonymous
Post 04/15/2026 10:04     Subject: Is it worth paying tax via credit card?
Anonymous wrote:It's only worth it if you are using it to get a sign up bonus for a credit card, but nowadays points are not worth nearly as much as they used to be.


Yes this is how we do it- line up a new card for when taxes are due, use that to hit the bonus quickly.
Anonymous
Post 04/15/2026 07:23     Subject: Is it worth paying tax via credit card?
It's only worth it if you are using it to get a sign up bonus for a credit card, but nowadays points are not worth nearly as much as they used to be.
Anonymous
Post 04/15/2026 03:24     Subject: Is it worth paying tax via credit card?
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.


How do you both get enough PTO to take 6 vacations a year?


Be a senior exec that has the flexibility to work whenever and from wherever (e.g., while still in business class on a flight from IAD to HND).

Also, learn how to flex your time within a twice-monthly pay period. Example: we fly IAD-HND on Saturday 06/13 landing in Tokyo on 6/14 at 3:55pm. We stay in Tokyo for 7 nights. We fly HND-IAD on Sunday 6/21 landing in D.C. on 6/21 at 3:50pm. Flying over two weekends means we need only 5 days of PTO, but this trip is over Juneteenth (Friday 06/19) which means we only need 4 days. By flexing time and front-loading hours in the 06/01-06/15 pay period we can avoid using PTO on Monday 06/15. By flexing time and back-loading hours in the 06/16-06/30 pay period, we can also avoid using PTO on Tuesday 06/16. And, voila, we really only need two days of PTO to enjoy a 7-night luxury vacation in Japan.

Repeat this 5 more times and use only 12 days of PTO total for 6 trips. Have shorter 4-6 night trips and use even fewer days of PTO.

I feel bad for the people too stupid to figure this stuff out….
Anonymous
Post 04/15/2026 02:56     Subject: Is it worth paying tax via credit card?
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.
Anonymous
Post 04/14/2026 21:33     Subject: Is it worth paying tax via credit card?
Anonymous wrote:The humblebragging on this thread is too funny.


Only one idiot taking 6 vacations
Anonymous
Post 04/14/2026 21:25     Subject: Is it worth paying tax via credit card?
The humblebragging on this thread is too funny.
Anonymous
Post 04/14/2026 21:16     Subject: Is it worth paying tax via credit card?
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.


How do you both get enough PTO to take 6 vacations a year?
Anonymous
Post 04/14/2026 20:53     Subject: Is it worth paying tax via credit card?
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.
Anonymous
Post 04/14/2026 17:56     Subject: Is it worth paying tax via credit card?
Is that card giving you 2%+ back? Seems like Feds will charge you 1.75% to use a credit card.
See the % for every type of payment on their website.
You should have accounts with state and Feds. Pay on their websites after e-filing, but don't be late.
Anonymous
Post 04/14/2026 17:45     Subject: Is it worth paying tax via credit card?
Anonymous wrote:It's really very easy to pay the IRS through a withdrawal from your bank account and there are no fees.


That's what I always do and will do now as well. I thought the cc fee was much less, like 1.75%. Not worth the trouble.
Anonymous
Post 04/14/2026 17:33     Subject: Is it worth paying tax via credit card?
It's really very easy to pay the IRS through a withdrawal from your bank account and there are no fees.
Anonymous
Post 04/14/2026 17:31     Subject: Is it worth paying tax via credit card?
I don’t do it because I don’t want to pay extra fees (3%?) that comes with it
Anonymous
Post 04/14/2026 17:31     Subject: Is it worth paying tax via credit card?
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.
Anonymous
Post 04/14/2026 17:30     Subject: Is it worth paying tax via credit card?
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.