Not a lawyer, no legal advice, just what I'd do in your situation. 

WS is 100% legal in SC 

Legally, it's mostly like renting by the room so there are no extra hoops to jump through in 90% of the country.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

@Pat QuarantoTo sell a property, assess its value, negotiate a fair price, and secure a legal deal.

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.