If you don't feel up to a fairly significant repair, I'd walk.

Would artificial grass be considered a negative by renters - i.e. too tacky or 'low-rent' in a fairly high rent rental?

Well, you can be fairly confident in your cash flow, at least for a few years.  

We are at $21 SF, internally we see that as fair market value.

I believe that’s a Fair Housing violation too so it stands for all states.  

If your goal is to move from management-intensive real estate to laissez-faire real estate, there are plenty of ways to invest in real estate passively and avoid the large capital gains.Your CPA should also have reminded you that if you die owning real estate, your heirs inherit the property at a stepped-up basis.

Fair pricing, with timely & quality work! 

It's possible that they heard a little bit too much from the fair housing commission and are now considered a "professional tenant"Usually these people will not listen keep withholding payment, and take advantage of the system as much as possible.

My personal taxes involve fairly complicated investments that also require multi state filings.  

I don't think it is fair that I have to go through the entire process of marketing and showing the unit again.