hey @Matthew Toporowski, at the least I would check their financials/tax returns to see how profitable they are (which translates into how easy it will be to pay your rent).

Would it be advisable to move my LLC from Florida to Delaware also in the event I need to go to court to recover the loan would an llc in Delaware be better? 

That question cannot be answered in definite terms. 

But if you are truly wanting to be an investor, time is money.

Especially since the market might be turning. 

Software can be very subjective.

Be very careful when it comes to vacation homes you need to be very experienced to be able to calculate the exact net cash flow. there is so many expenses that you might not understand, in other words you need to do your homework before touching any vacation rentals especially with the pandemic .

If you live below your means you should be able to save enough for this. 

Any insights or advice would be greatly appreciated!

I will be taking a residential loan from my TSP since by my calculations that would save me a lot of money on interest and give me good equity.