In a seller's market, home prices typically increase due to limited inventory, while in a buyer’s market, prices tend to be more negotiable.

It does feel like there is likely a major market correction coming, but due to limited inventory of vacation-rentable units in Maui I feel like I should be somewhat more protected from the effects of said recession.

If you've enjoyed a lot of appreciation in the value of your primary home, you may want to start a timer to sell before losing the "lived in the house for 2 of the last 5 years" capital gains exemption (limited; not infinite, but big).  

Additionally, if you have too many personal use days, losses may be further limited by the Sec. 280(A) vacation loss limitations. 

Some people go to Lake Lewisville/Dallas/Grapevine, but I don't hear about them spending the night and there are pretty limited options right on the water.I still hear a few people going up to Broken Bow/Hochatown, but that talk is way way down since about 2021. 

This limited inventory will likely continue to drive prices upward.Sales - Median $/SF by MonthThe $/SF increased slightly MoM, bucking the seasonal trend.

With your skillset and limited finances, it might be great to be a small partner on a deal with another flipper or be some of the work on the deal so you can see how it feels time wise.

As stated above, this limits your conventional loan options, and means your rate will be higher with either a Conventional Loan or DSCR loan once you do the refi! 

So if you are selling a property in a given year, it might be worthwhile to talk with your CPA and see if selling some stock at a loss would be helpful (since otherwise capital losses are limited to $3,000 as Joshua mentioned). 

All that combined with limited building and no state income tax there is positive rent and appreciation.