You obviously want to shoot for a high amount, I always feel comfortable after mortgage, insurance, taxes, and misc expenses (estimate) that anything over $300-400/month is good cash flow.

They also admittedly have approved similar claims in the past, so I have requested copies of all requests made over the four years the condo building has been in business (only 12 units, so it can't be too much).I won't really be able to get an appropriate estimate without ripping up the floor boards, so should I just choose a reputable contractor and then take them to small claims court?

I estimate $80K in pocket after all is said and done.  

The property itself could bring in a conservative estimate of $2800 a month once all units are fixed up, but I would be sacrificing $400 of that by living in it of course. 

They're using Zillow to estimate the value of a home in the country?

We have given USAA everything they've asked for including all paperwork, police reports, contractor's estimates and other supporting documentation (e.g. ownership of stolen appliances).

Zillow rent $2100, zillow value estimate $346K and change. 

I recently graduated from Montclair State University as a Business major, and have to decided on real estate as my vehicle for accumulating passive income.

Also, I have had wholesalers provide me with horrible rehab estimates where they overlook some important issues (like an $8k electric wiring update).

In Georgia, we send off "estimated" charges from the move out.