I have gone ahead with painting Navajo White for all the walls, and Ultra White for the trim and plan to use this color scheme throughout all the units eventually.

I have yet to get under contract since attempting to since labor day, but I am in no rush.

Ask yourself, if it was Christmas Eve and there was a major problem at the property, who would rush to deal with it and who would want to push it off until tomorrow?

Welcome to the community, you are already light-years ahead of most people with getting into real estate at your age.

(long response ahead)First off, I just want to say I see you—and you're doing the best you can under some tough circumstances.

You've (likely) got another 60-80 or more years ahead of you.

Honestly, reaching out to property managers is a great idea, and I’ll go ahead with that.The problem is that a good contractor is sometimes an asset in itself that can be hard to share.  

He is FAR FAR ahead of you!

Part of me wants to turn down the application due to the concerns around this criminal history, the other side of it is it is a tough market currently and slow season ahead and insisting on rejecting the application would likely create serious rifts with my property managers (whom I have generally been fine with otherwise) as they are pushing back on rejecting due to criminal history from years ago.  

If everyone was following that same rule, I’d gladly do my due diligence ahead of time.