We painted the outside, cleaned up the backyard, changed the fireplace, changed kitchen countertops and backsplash, added accent wallks.

When you take all five together they should paint a picture, but I also mentioned your gut is important (not your emotions).

What color are you painting your stock cabinets?

Paint is not rocket science, and he asked if I had any work that needed doing, so I let him do the paint job instead of my painter (accepting in my mind that if he didn't do a great job this was going to be charity).

Patch, sand, prime and paint the holes and paint to match the wall.

We have minimal resources as far as money goes, but we have a relatively long list of upgrades (window treatments, hardware, light fixtures, paint, etc).

Quote from @Jim Reynante: After owning properties C/D neighborhoods with high crime statistics, I have experienced all of the things that go along with it: 1) High turnover rate; 2) Tenants that don't care for the property; 3) Little/No appreciation in home value; and 4) High Crime Rate (burglary, vandalism).I am pretty tired of fixing broken windows, fixing broken doors/locks, and painting over graffiti.

You can use Zillow or rent cast along with others to paint a picture of the area where you want to invest. 

He received quotes to remove the texture ceiling, paint the interior, purchase and install new kitchen cabinets and counters (including completing the design), picked out 2 floorings to get quotes which will be provided this week, and determined furnace is beyond saving (I will likely get HVAC quote for him).  

We saw a large influx of section 8 re-inspections (and even new inspections) coming back and saying that the properties needed fresh paint, new countertops, etc.