Based on the photos we wouldn't recommend a full paint job.

Just remember to consider the local job market, population growth, and rental demand when making your decision.

My wife and I both have decent paying jobs, but after paying rent, vehicles, student loans, etc, there’s not much left over for saving, let alone 20% down.

If they can do the job for that price, you should hire them immediately!

New roof, siding, soffit, fascia, flooring upstair, repair fencing, yard work/landscaping, new flooring upstairs, new vanities, kitchen remodel, new paint job What was the outcome?

Consider emerging Sunbelt markets like Phoenix, Tampa, or parts of North Carolina (like Raleigh or Charlotte) that continue to see high migration and job growth, driving both appreciation and rental demand.

.: Quote from @V.G Jason: Great job.

In other words, the cap rate becomes fairly meaningless upon transfer.Your job is to assess whether or not you can make a good profit after buying the asset at whatever the sale price is. 

I understand equity and cash-flow are related, but what I mean is that I don't need the cash flow right now as much as I'd like to build a strong portfolio that can cash flow even more later on.I've owned a single-family rental for 4 years, but on mulitple fronts I felt like I've done a poor job self-managing it, so this Fall I picked up the Turners' book on managing rentals and that's what led me here to Bigger Pockets online.

You are 20 years old and don't even know what it's like to work the same job for five years.