Don't count on appreciation in the next few years to cover your month to month losses.

You just need to cross out the area that says "not assignable" 

You need an Indiana lawyer to meet him face to face and put the squeeze into him.He is not following the rules of the contract and must be made to heal like a dog.Don't be afraid of litigation,that is what he is counting on.He will probably crumble when he sees a pit bull of a lawyer in his face demanding documents and threatening lawsuits for fraud and maybe theft of materials.

Do your own internal rent survey of bed bath count and similar sq footgage that is current indicator

Taking legal action has crossed my mind a few times. 

Hard work is not working 100 hours, it is making the hours you work count for something.

Your repairs will be out of pocket and can be counted as either expenses or treated as capital expenditures adding to your basis (talk to CPA who knows rental real estate).  

Also, in the kitchen there is a radiator taking up a decent amount of space that could be used for lower cabinets instead... the kitchen is pretty small so all area counts, what do you do?

NYC might bot be the best place to start if you're a newbie but I wouldn't count NYC completely out. 

I'm looking to maximize monthly cashflow, rather than counting on any appreciation.My price point is in the $50k-$100k range.