@Scott O'Halloran Small banks look at a number of items when underwriting a rental portfolio:1.

I find tenants do not bother you as much with little items and will go the extra mile in handling issues themselves.

Get 3 bids (you may want to start with one and get a list of work items, then get the other two to estimate the same work - don't share pricing!)

However, unless you do the work THEY demand you do (fyi be coachable to every item... which could conflict timewise with your job, family life, other commitments, etc) you don't get a dime back.

Also if you call in a few contractors to give itemized bids you will start to get an idea of what things cost and at least have ballparks for items like a kitchen, bathroom, a roof. 

You could have damage and items stolen everytime you do something.This is a marathon not a sprint. 

You might be better off if you just interview property management companies, and see if they would give you a copy their lease, i am not saying to plagiarize it, however there might be specific items in that document that an attorney would not know just because that is not what he does on a daily basis.  

There was plenty of other items as well.Next time I will have a more regimented evaluation structure.

I personally would try to use line items to break this down (ex. snow removal, landscaping, etc).  

I can't remember anymore what it was, but there was one item that we were just like "what the hell?"