The biggest issue we have is educating our "young" student tenants that with the exception of toilet paper "if you did not eat it, do not flush it" ... those idiotic personal wipes are the worst (talk about a "solution" looking to create a problem/need and market).  

Fast forward half a year, and rents & statements are coming in months late and soon stopped coming period.As I didn't have a contract, my gut reaction is that I should just eat the loss and move on with a lesson learned. 

The first thing we always do is get 1 bathroom completely finished, then you can sleep on a blow-up mattress and eat pizza till the kitchen is ready. 

But I'm stuck eating the 20k in damages between the carrying costs of the property during the months it was off and having to re-do a fully finished 2-week old basement.

In this case, I had to eat the cost for several reports.

This unit is not in a particularly great area, but that said it is 2 blocks from the city police station and 1 block from the city hospital as well as some nice places to go out to eat/for drinks in walking distance.I'm estimating a rent price of 500-700 a month and using the 2k per month as the low ball for evaluating this piece of real estate.  

try to find listings were these are update or near new.. if you do that its not mandatory to buy a completely fresh reno.Plus most turn key  companies simply don't have 4 plex's  they deal in SFR's  you may find some that work the really rough areas of the mid west and sell low end duplex's but those will eat your lunch over time.I think you should step back and reassess.. 20k simply is not enough cash to go out and make this work.. at least IMHO

The Rehab could be a lot more (or less) and the Closing/Holding costs will eat up more than you think. 

If she wasn't your girlfriend, you wouldn't think twice about partnering with someone with her attitude("but she doesn't like to be on a schedule").You are hungry and trying to eat everything in sight; she is pecking at her small side salad.

That mean that she has a severe mental condition, (bipolar disorder, major and chronic depression, severe eating disorder ect. ) she then has to demonstrate that the cat performs a service that helps her condition.