Are there any things I can counter with or have buyer cover (closing, taxes, fees, etc)?

sarcasm: check the local adverse possesion laws :)Seriously: if it looks like you could strike a deal with him, split or cover the locksmith fee with him to have keys made (by his request).

I sent the $2000 cleanup bill to the tenant for negligence and she is refusing to pay claiming that my homeowners insurance should cover "old pipes." 

If he doesn't want to use debt to leverage his current sum, it's going to be a slower climb, but with less risk (ie if a property he buys with cash sits vacant, he doesn't have mortgage payments to cover).

Do you have a picture of the outside of that window?

When i mention we need to come up with special assessment to cover the damages he says he won't pay and other members won't pay either. 

But I did see you have "misc" at 10% so i guess that about covers it.

Based on some insight that I have been fortunate enough to come across, a security deposit most often does not cover all of the damage to the property.  

If you're ok with that kind of return you should be relatively safe and have operating expenses covered with that rental rate assuming you've done the diligence (it seems correct though since I know the spring, tx area somewhat).

From what I understand, a short sale is an agreement between the current “defaulted homeowner” and lender to sell at a price that will attempt to cover the mortgage, but once put under contract or sold does the “defaulted homeowner” have the option to recapture the home in a short sale as they may in a foreclosure?