Especially if the market slows down.With our home, the kitchen was good, but it had carpet and nasty bathroom tiles, so we did that, repainted, and put in new toilets from Costco, and the over $14K we spent on that seems to have added about $30K already to the home value, probably more in the future as we have long-term appreciation. 

But, we want to repaint correctly.

I know I will have to repaint the inside of the house too. 

Start fresh, repaint the unit, put it in the lease that smoking is not allowed for the next tenants. 

PM said that upon following up it's due to personal lives of the tenants(moving, new job, getting married, etc)I did have one major repair last year (exterior stairs repainted and treated that cost $8500 and $375 project management fee)Total Annual Income = $57,060Total expenses(everything except Principle and Interest) = $35,72562.6% of the rent is being spent on expenses - I've read that this is around 50% optimally.This seems all pretty high.... 

You will need to repaint most of the time on move out.  

If you are having so much trouble with this contractor, then don't use him again or just pay him for what he has already completed and hire someone else.I don't know what exactly what you had him painted and why, but if say for example you are only replacing part of siding, etc then repainting those parts to the original color is very common.

I'll be retiring and am looking for steady, less hands on cash flow.My question is, currently in this area, will it be smarter to keep the tenants in residence and sell as an investment property, or move the tenants out, repaint, and sell as a home or investment property?  

I assume it'll have to be cleaned and repainted. 5) Should we refinance to a 15 year mortgage to get a lower interest rate?

The apart was repainted before we lived in but, I beleive this is a normal wear and tear, I did not break any wall, window or cabinets...