I would love to get a condo down in Miami to have a as a forever rental, but it's just so hard for me to pull the trigger.

Quote from @Scott Trench: I know that anytime Trump's name is mentioned, someone gets triggered.

Tax StrategyWhile liquidating the brokerage account may trigger capital gains taxes, strategies like staggered withdrawals or tax-loss harvesting can help minimize the impact.

However, to my understanding, a 1031 conversion of an investment property to your primary residence after a safe harbor of two years does not trigger a tax event.

If I had an answer to my money issue then I would quickly pull the trigger on a good deal. 

My Wife and I are going to pull the trigger in 2025 and are looking in the Central PA area to buy our first STR.

Ensure that the mortgage is assumable, and confirm that there are no due-on-sale clauses that could trigger the full loan balance. 

  ( Maryland )  Small parking lot 12 cars plow and salt $450 . 2 in trigger Costs are regional for sure 

Once you find a good property and all the numbers make sense - pull the trigger.

From my experience working with over 400 investors, avoid transferring your home into an LLC (it can trigger loan issues), be mindful of capital gains taxes when selling, and ensure your debt-to-income ratio allows for your next purchase.