Most if not all of these properties require SIGNIFICANT cap ex rehabs and conventional financing won't touch them; you'd likely need to go the hard money route at 10-12%, 2 points, 12-18mon turn around.

You may be required to make estimated tax payments when the property sells.It depends on what your 2024 total taxes due were and 2025 estimated total taxes / withholding / estimated payments are.If you pay in atleast 90% of the current year tax or 100% / 110%(Depending on 2024 income), you are normally considered good.You may want to consult with an accountant for more clarification.

Since you're in Destin, you might want to check with local firms that have experience with STR-heavy communities, as they’ll be familiar with the risks and requirements.

Most people think real estate investing requires huge capital, perfect credit, or bank loans—but that’s not always true.

There are more complicated strategies to maximize larger listings that involve having like multiple listings for same property and do individual room rentals when it is slower and then for larger length stays, larger groups, and more desirable dates you'd book the whole space, but I think its easier to just do two separate. 

Now, some states require an attorney to review contracts. 

FHA loans are designed for primary residences and require the borrower to be an individual, not a business entity.

Its a great idea, but you will need to consult the township in order to understand their requirements for liveable space.

Unless you have time, desire and knowledge, hiring a property manager sounds like the right option.

If you don't have a US-based bank account, I would get one as that's a requirement by most lenders.