You picked a great community to join.. have you checked out local comps to gauge the market vibe yet?

You will want to check your laws first, it is illegal in FL to require renters insurance.

You will need to check with the city/building inspector to determine your options first.

I recommend checking the areas near University Circle for that reason, but there are some spots not far from there that can be rough, so do your due diligence.

For durability check the max weight and look for performance fabric options. 

If they're doing anything another tenant would complain about I send them a written warning and the minute another tenant complains is when I'll double check to see if I can file eviction for that specific thing and give the tenant three days to knock it off. 

You might want to double check he understands the scale of the project you're asking him to do. 

Minimal changes to effect common entrances, no major shifts in load bearing, easy plumbing changes for wherever the new kitchen would be... it's a lot of boxes to check. 

The only item I would suggest is double check the payment terms of the your HELOC... in particular, can you pay interest only or are you required to pay a portion of principle each month on the amount utilized.

I've been checking HOA CC&Rs to make sure they allow short term rentals.