@Renzo Figueroa Please make noteThe peak season for tourism and Airbnb stays in Jacksonville, Florida is typically in the summer months, from June to August, when visitors flock to the city's beaches.

All visitors will still get up to three free hours, after which parking will cost $18 per entry.

Rather than deplete the tax-sheltered IRA, you could continue to grow it and only distribute to yourself the minimum amount required, or perhaps a bit more here and there as suitable.

The next day I get a text, that a “family member” just happened to stop by and noticed “new temporary” visitors in the bottom apartment and there are new laws in the city starting June 1st for short term rentals.

This means that it's in a location that is known to be suitable for short term rentals and is allowed by the HOA.

Beyond a local CU or bank the next best way to find a suitable location is probably a referral from your RE broker or listing broker.

But, baring some Disney type of big attraction coming to the area, I think it’s safe to say 2019 visitor counts, plus say maybe an additional 20% due to awareness of the area post COVID, is all we can expect.  

It would be best for you to go over a suitable business structure and tax implications.

I can't know this for certain, of course.Not sure if this is worth pursuing with a lawyer or chalking this up to a lesson learned (be very careful buying properties in a wet area with finished basements, ensure it is suitably water-proofed).

It will help visitors read the table and understand what kind of coverage you provide for the areas that they are interested in.Your IT team team should be able to do that fairly easily!