The only time I've seen this turn into an issue is if you offer to pay for the flooring and then the tenant comes up with more requests every couple of months (e.g. new toilet, different color paint, new washer/dryer, etc.) 

I love the idea for the lighter colors, do you think the SW agreeable gray with white trim will be good?

I gave too much control up without having worked with this guy before, and several aspects of the construction work went off course, including the kitchen design and color pallette.

The process looked like this:  TSP wash and degrease area by switch plates, scrub baseboards, scrub angle turn valve, scrub top of vanity light bar, scrub top of door frame...then cut in ceiling of each room, then remove exhaust vent cover and vacuum around it, then paint ceiling of each room, then paint baseboards, then cut in wall color (which actually means entirely paint some tight areas), then apply first coat of wall color, then apply second coat of wall color, then hit the cut in areas again where there aren't two coats. 

Painted both of the bedrooms I rented out (one of them was a horrendous blue color) and did some cheap curb appeal fix-ups (mulch, cleaning, etc.)!

Any color on how this has worked for you?

And yes, I really do not get a good feeling about tatted head to toe women and people with weird hair colors and piercings.

Dark colors. 

To that end we plan to change the color.

In my market, that is generally the "middle-class" income or blue collar and lower white color neighborhoods, etc.