In 2nd position, with no equity, with an undesirable property, it could be a lost cause to milk it much further to recoup losses. 

You can walk into a grocery store, ask for the manager, say you want 1G milk for $0.42.

I do know the area/comps pretty well (but she knows it better) and I am well aware that I do not know all of the costs involved (but I am learning from yall so that I won't be a jerk, but also want to milk this deal for what little value that there might be).

Milk that cow!

It sounds like he's milking this property for all it's worth or maybe there are health problems where the owner needs the money and just can't afford to put it back into the property.  

We used to get steel milk cans from a dairy down their too and use them for all kinds of cool stuff. 

Money Mustache, both are interesting sources to pick up some tips on cutting expenses.I would start off building your buy & hold portfolio and continue to educate yourself.  

Recall the analogy of the two frogs in the milk bucket.

Otherwise, you could just let anyone in the unit and milk it until they stop paying, boot them, collect your money from insurance, and move on. 

If you want some ideas, read my blog, mr money mustache, paula pant or one of the many blogs, podcasts, etc out there to help with spending of money, or how to cut back on the spending of money.The money podcast here on BP is FABULOUS!!!