Anonymous
Post 07/17/2025 14:42     Subject: Ideas for Vacation-income generating homes locations with all year around use

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:I think you are unfortunately a decade or two late for your money making scheme. The average chump won't be able to afford his own mortgage by next year, let alone a vacation.


Speak for yourself. Not everyone is poor


No, but the people who want to rent a condo for a week in daytona beach are.

Also, do your research and look at property records in places like Hilton Head. Notice any patterns? Still want to buy?


What is the pattern in HHI?
Anonymous
Post 07/17/2025 13:40     Subject: Ideas for Vacation-income generating homes locations with all year around use

I knew a couple who retired early with two rental properties and no primary property.

They had a house at Hunter Mountain NY right by Mountain. Hunter is a second tier ski resort at best but has a very active bar scene and popular with single people in Manhattan as close enough to go every weekend and on three day weekends. Strong winter rental market. For whole season.

They also had a house in Westhampton NY in Hamptons. Closest to NY part of Hamptons. Another place very strong rental market for whole season.

The would rent out Hamptons house whole summer season and Hunter Ski house whole winter season. They would live in the houses off season. Upstate NY is very beautiful in summer and the Hamptons are still pretty nice and active after crowds leave.

Plus no tenant headaches as a full season least, an agent nearby to manage issues and they in off season can do whatever needed easily as lived there.

I thought it was smart.
Anonymous
Post 07/17/2025 11:39     Subject: Ideas for Vacation-income generating homes locations with all year around use

Anonymous wrote:
Anonymous wrote:The idea that someone would buy real estate in florida in this day and age is INSANE.

Besides the political stuff, the fact that it will be uninsurable, and uninsurable for the reason that the state is a literal disaster 8 months of the year.

What are you even thinking?


Rep Donalds will almost certainly be the next gov and solving the insurance crisis is his #1 focus. If I had some extra cash I’d try to pick up some property in 2026/2027 when the FL market bottoms to take advantage of the boom once the insurance crisis is fixed. Also if you pay cash for the house outright the insurance is significantly lower. We pay $3K/year for home and flood insurance for a 1980s duplex 50 ft from the ocean.


LOL. You think Donalds is going to fix it. How deep down the MAGAt hole have you gone?

If you want a property along the beach in the South, Florida is the last place to look.
Anonymous
Post 07/17/2025 11:34     Subject: Ideas for Vacation-income generating homes locations with all year around use

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:The idea that someone would buy real estate in florida in this day and age is INSANE.

Besides the political stuff, the fact that it will be uninsurable, and uninsurable for the reason that the state is a literal disaster 8 months of the year.

What are you even thinking?


Rep Donalds will almost certainly be the next gov and solving the insurance crisis is his #1 focus. If I had some extra cash I’d try to pick up some property in 2026/2027 when the FL market bottoms to take advantage of the boom once the insurance crisis is fixed. Also if you pay cash for the house outright the insurance is significantly lower. We pay $3K/year for home and flood insurance for a 1980s duplex 50 ft from the ocean.


There’s no way he’s going to “fix” the insurance market. Not when 100 year storms come every three years. Florida is a money pit and the state can’t backstop the market indefinitely. My family who has been there for more than 100 years is moving north. But hey, I guess there’s a sucker born every minute. Good luck with your soon to be underwater property.


Well in Florida at least older condos will take massive hit or repairs and increasing reserve funds now. By 2027 the older condos may bottom and the bulk of assessments and repairs done. Or at least you will have financials that now show current reserve funds, work done, you can make a decision on. By 2027 when you have 2026 financials on those older florida condos you will know what you are buying at least.

People who bought in a rush in 2020/2021 got hit with huge assessments.
Anonymous
Post 07/17/2025 11:33     Subject: Ideas for Vacation-income generating homes locations with all year around use

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:The idea that someone would buy real estate in florida in this day and age is INSANE.

Besides the political stuff, the fact that it will be uninsurable, and uninsurable for the reason that the state is a literal disaster 8 months of the year.

What are you even thinking?


Rep Donalds will almost certainly be the next gov and solving the insurance crisis is his #1 focus. If I had some extra cash I’d try to pick up some property in 2026/2027 when the FL market bottoms to take advantage of the boom once the insurance crisis is fixed. Also if you pay cash for the house outright the insurance is significantly lower. We pay $3K/year for home and flood insurance for a 1980s duplex 50 ft from the ocean.


There’s no way he’s going to “fix” the insurance market. Not when 100 year storms come every three years. Florida is a money pit and the state can’t backstop the market indefinitely. My family who has been there for more than 100 years is moving north. But hey, I guess there’s a sucker born every minute. Good luck with your soon to be underwater property.


The problem with the insurance market isn’t the storm intensity or frequency by itself, it’s the “assignment of benefits” issue. You can absolutely fix that issue if you buck the Tallahassee swamp lobbyists.

https://news.fiu.edu/2022/the-big-reason-florida-insurance-companies-are-failing-isnt-just-hurricane-risk-its-fraud-and-lawsuits

Anonymous
Post 07/17/2025 11:31     Subject: Ideas for Vacation-income generating homes locations with all year around use

You do know with one law change they can stop short term rentals.

I now a guy who bought his second home in Long Beach, NY. It has beach all summer, but LIRR to NYC is in town 45 minutes to Manhattan and short ride to US Open he likes Tennis and JFK airport. But rentals less than 30 days illegal. People still do them but you cant relay that income if someone complains.

He bought there as he retired to Florida. But he wanted a place to go to get out of heat of Florida in summer, be on beach, take train to NYC as wife likes to go to plays, museums and restaurants and he liked to go see sports events sometimes. But no way he wants to pay NY taxes or stay in NY all winter.

Long Beach NY sounds crazy but there are not many beach towns busy all four seasons.
Anonymous
Post 07/17/2025 11:29     Subject: Ideas for Vacation-income generating homes locations with all year around use

Everywhere I want to be, that has real income potential, isn't affordable for anyone but the top 1% anymore. Kinda sad.
Anonymous
Post 07/17/2025 10:58     Subject: Ideas for Vacation-income generating homes locations with all year around use

Anonymous wrote:
Anonymous wrote:The idea that someone would buy real estate in florida in this day and age is INSANE.

Besides the political stuff, the fact that it will be uninsurable, and uninsurable for the reason that the state is a literal disaster 8 months of the year.

What are you even thinking?


Rep Donalds will almost certainly be the next gov and solving the insurance crisis is his #1 focus. If I had some extra cash I’d try to pick up some property in 2026/2027 when the FL market bottoms to take advantage of the boom once the insurance crisis is fixed. Also if you pay cash for the house outright the insurance is significantly lower. We pay $3K/year for home and flood insurance for a 1980s duplex 50 ft from the ocean.


There’s no way he’s going to “fix” the insurance market. Not when 100 year storms come every three years. Florida is a money pit and the state can’t backstop the market indefinitely. My family who has been there for more than 100 years is moving north. But hey, I guess there’s a sucker born every minute. Good luck with your soon to be underwater property.
Anonymous
Post 07/17/2025 07:00     Subject: Re:Ideas for Vacation-income generating homes locations with all year around use

Anonymous wrote:Anywhere on 30a. As long as you have a few million to spare.

https://redf.in/0UEs4Y


Having owned a home in Seaside for many years, I would be more apt to buy this place in Seagrove.

https://www.zillow.com/homedetails/18-Bay-Laurel-Ln-Santa-Rosa-Beach-FL-32459/250740817_zpid/

Seaside is now insanely priced and has so much HOA drama, politics and lawsuits, not worth it IMHO.

The price point for the above listing makes it more economically viable, plus it’s in a small private gated community (walled off from the hordes of tourists) but still bikeable/walkable to Seaside square, public beach and Publix).

Of course, it looks pretty dull compared to your listing but can be inexpensively transformed into a more beach cottage vibe.

30A offers great rental potential, but it does get cold from Dec - Feb. it has the same insurance challenges most of the state has, but much of the area doesn’t have flooding issues (unless you live on canal etc). Hurricanes are still an issue but tend to hit a bit further East- Panama City and the big bend.
Anonymous
Post 07/17/2025 06:11     Subject: Ideas for Vacation-income generating homes locations with all year around use

Second Taos.

Vail and Aspen. There is demand year-round but the premiums people pay during ski season are outlandishly high.

Hawaii
Anonymous
Post 07/17/2025 05:32     Subject: Ideas for Vacation-income generating homes locations with all year around use

Asheville
Denver
Anonymous
Post 07/17/2025 05:31     Subject: Ideas for Vacation-income generating homes locations with all year around use

Anonymous wrote:
Anonymous wrote:The idea that someone would buy real estate in florida in this day and age is INSANE.

Besides the political stuff, the fact that it will be uninsurable, and uninsurable for the reason that the state is a literal disaster 8 months of the year.

What are you even thinking?


Rep Donalds will almost certainly be the next gov and solving the insurance crisis is his #1 focus. If I had some extra cash I’d try to pick up some property in 2026/2027 when the FL market bottoms to take advantage of the boom once the insurance crisis is fixed. Also if you pay cash for the house outright the insurance is significantly lower. We pay $3K/year for home and flood insurance for a 1980s duplex 50 ft from the ocean.


3k a year to insure that seems insanely low given the risks.
Anonymous
Post 07/16/2025 20:58     Subject: Ideas for Vacation-income generating homes locations with all year around use

My cousin has a place in Taos that is in great demand year round. Some place like that would be a good option, but far.
Anonymous
Post 07/16/2025 19:37     Subject: Ideas for Vacation-income generating homes locations with all year around use

Anonymous wrote:
Anonymous wrote:The idea that someone would buy real estate in florida in this day and age is INSANE.

Besides the political stuff, the fact that it will be uninsurable, and uninsurable for the reason that the state is a literal disaster 8 months of the year.

What are you even thinking?


Rep Donalds will almost certainly be the next gov and solving the insurance crisis is his #1 focus. If I had some extra cash I’d try to pick up some property in 2026/2027 when the FL market bottoms to take advantage of the boom once the insurance crisis is fixed. Also if you pay cash for the house outright the insurance is significantly lower. We pay $3K/year for home and flood insurance for a 1980s duplex 50 ft from the ocean.


The insurance issue isn’t fixable. Some temp patches can get the system functioning again but it will never be cheap again and it will only be a matter of time before everyone bails.

The climate is changing and the building patterns in Florida are not sustainable. It’s too low, too exposed and too poorly built.
Anonymous
Post 07/16/2025 17:41     Subject: Ideas for Vacation-income generating homes locations with all year around use

Looking solely at the year-round aspect and not analyzing profitability:
- Florida beaches, like you said. Fort Lauderdale, Sarasota, 30A, and the keys are popular destinations.
- Mountain areas with skiing in the winter and mountain biking, rock climbing, and other sports the rest of the year.

Check out other tourist destinations. Not sure about the year-round viability of Savannah, Charleston, etc.

But I caution you to look at a second home and an investment property as different things and not try to combine them. For an investment property, look at where you can make the most money (or a non-RE investment). Then use that money to fund either a second home or vacations.