If you a selling the property then a fresh coat of paint can go a long way.  

Also see @Chris Clothier's BP Post on 20 Questions to Ask Before Hiring Property ManagementA few comments/questions (perhaps from a PM perspective):Most (all?)

I was 16 and making 400 bucks a month for driving to the store twice a month and picking up fresh brownies every morning to distributing them to sellers.

I'll be selling to the fresh faced investor as soon as I can.

This is surly why you are feeling so constrained from a cash perspective. 

The payment shouldn't increase my debt-to-income ratio much because of my high salary and I am quite frugal in that I save 50%+ of my income and have little other expenses other than rent so from my perspective I'm still safe.Of course, underwriters have different opinions so I don't want to screw my future self by financing an auto to stay liquid only to find out in a few months they would want me to pay it off before getting a mortgage.

Larger properties are easier from a management perspective because you can hire a very sophisticated and experienced manager (the trick is finding and vetting them).  

These people, the ones in distressed situations, need to move on and re-invent themselves, as they move on from a problem house and into a fresh new future.Because you've been in rough situations, you will have empathy. 

Going to be re-freshing all the units if I buy it.I know it varies by market, but what apartment upgrades have given you a solid ROI?  

Do not discount your gut feelings when meeting with a perspective tenant.