He did not seem remotely appreciative of my offer.This tenant has been resistant to my policies from the beginning, and seems to take any action on my part as aggressive.

Chipping and flaking paint, thats got to be taken care of.  

I am having the apartments painted and after painting it the contractor came back the next day to find that in certain sections the paint had started to run.

He already did the inspection (nothing major)It is a four plex in Lakewood, Ohio for 125k and i'd say needs about extra 10k (exterior paint and some more repairs)My biggest issue is I know that I'm as a renter would prefer to rent for the same price a 2 bedroom apt in a nice building in the same area instead of renting a unit in this 4plex.

One thing I've found is, the harder I try to push my spouse, the more he resists.

You could try it in this order:1) Offer full deposit back if she moves no, questions and no need to worry about rent as long as it's decent when she's out.2) Resistance?

(HVAC and water heater are end of life, plus needs interior/exterior paint, flooring, and other significant but not major issues). 

We have rented our home so quickly between renters, we rarely have the time to slap on another coat of paint.  

It would be a good ideal to paint all treated areas with a stain blocking primer including the wood members, studs and sub-flooring if affected.

I will try to give some respectful inquiry as to what might be done on the sellers part to paint a better picture.