For our clients, we separate repairs into catergories: 1) Health & Saftey - highest priority to avoid lawsuits2) Property Preservation - don't want a $500 water leak repair to become a $5k repair later3) Government Required - for city & S8 inspections4) Marketing Negative Impact - who wants to rent a "purple" house?

Bump them up close to market rate, but consider keeping it 5-10% below market as an incentive for them staying. 

Is this a market better suited for single family LTR or mulitfamily?

Can I also charge him rent till I find a suitable tenant ( I intend to aggressively market the unit)?

I concur with @John Underwood's logic and agree with @Kevin Lefeuvre that Airbnb's solution works better (at least in my market).

Will the market continue to slightly favorite seller's in Montgomery?

How much money do I need , what licenses , where to look for off market deals?

My markets are North ATL, Greenville, SC & Spartanburg, SC. 

Do that in your post and ask what are you missing before deep diving and looking for numbers or marketing analysis.  

This works if the long-term market rent received on an appraisal can support the DSCR and you are buying vacant.