@Dave Rav I am looking to create a sort of side hustle myself.

On the positive side, I received an offer of $655 from a local investor for my boarded up Taj Mahal that Morris sold me for $61K. 

You get cold air running through the return, the hot air in the attic (especially in Valdosta, I know it well) condenses and runs down into the insulation and sheetrock.

We have been reading post after post for the past two years from (1) members who are fed up with the market (2) members who are having a hard time starting in a hot market and (3) members who have highly appreciated properties but don't have an alternative investment option if they were to sell or exchange.Deal flow is king in this market and you have to (1) put hundreds of deals through the funnel via marketing and networking or (2) you have to invest with someone who has it.I made a decision two years ago to do more of the latter...to start heavily vetting passive opportunities with experienced sponsors who have mature deal flow pipelines (i.e. deep broker relationships, industry leaders, full time staff dedicated to deal flow, consistent off-market properties)...while still casually vetting direct owned opportunities. 

If they catch you, they will drop you like a hot potato.You can rent to someone for a fixed term of 6+ months and then renew or extend on a month-to-month basis.

Too hot during the day?

Yes, Charlotte is hot but there are neighboring markets you may want to look into for greater yield (especially if your syndicating which it sounds like).

If the house is still mortgaged, I would only go with option 1 if the market is hot and I know it will sell so well that not only do I recoup the repair and rehab cost but make another 10K or more upon sale of the house.

One where he could live in one side and rent out the others? 

He doesn't counter back and accepts with a close in 14 days and 5K EMD that will be held by a title company on the other side of the state, 7 hours away.