Both bathrooms need a complete remodel as well as the kitchen, the ceiling in 2 of the bed rooms are bowed (previous roof leak that was fixed) so new ceiling drywall, appliances, flooring, and paint throughout.

Your pictures do not paint a picture of what I'm looking at.There is a renovated 2bed/1bath right around the corner for $1,050 and it has a decent floorplan.

Expect to remodel kitchen and baths and put new floors down, paint, knock down a wall to open the floor plan. 

But it gives you a chance to get a fresh start....make your place nicer, replace appliances, new paint, get rid of carpet and replace with LVP, Etc....

Power washing the exterior, repairing the driveway, and painting the front door What was the outcome?

The tenant fails to pay their last month's rent and leaves the place needing new flooring and paint.

Mortar, paint & bonding materials deteriorate leaving cracks, gaps, etc. which can be concerning to look at, but this is very often addressed with repointing.

In my area, they actually require a little more than the local municipality and lately have been especially strict on cracked paint because they were recently sued and lost.

Adding paint and replacing flooring is not going to add much value in the typical case.  

Just recently I undertook to do some significant painting at two of the buildings and my wife offered to help me out.