Also, if it is legal in your state/county, you need to ask for a higher deposit just to protect yourself in case, he decides to break the lease early a second time.Would I let him back in? 

Also, you LLC would disqualify you from using a residential loan since legal entities are not eligible for conforming residential loans.Usually, a HML would pay for a percentage of the acquisition and a same or different percentage of the reno. 

The HOA has to do reporting and there are some legal ins and outs that the person at the HOA management company is not so, how do I say, genius at fulfilling.https://entp.hud.gov/idapp/html/condo1.cfm 

Cost is mostly legal, with about $10K - $15K being average.

Concentrate on knowing local market dynamics, financial planning, legal and tax implications, and long-term objectives.

This is not legal advice.

Or legal advice - get with an attorney. 

There are sections of Dunedin and northern Clearwater that are Unincorporated (and therefore legal) that will be quite close to Tarpon and be a much better investment.

Also pretty certain you have to have the proper licensing in most area to do this kind of lease structure legally...

I know a developer that has successfully gone full cycle using the San Diego ADU law that allows max AduS to legal existing space likely over 10 times.