Seeking advice: sell 2 out of state properties using a relator?

[Sarah Young]

We have two rentals in another state, and are wanting to sell them and 1031 exchange them into something local. 

Property #1: We owe $193k. Realtor just did a CMA and recommends selling it at $225K. After the 6% commission, this would give us $19k max to walk away with (probably less after closing costs).

Property #2: We owe $290k. The tenant in the house has been asking us from day 1 if we would sell it to her. She is a former lawyer for the FBI, and is very high-maintenance, and honestly scares me. She has been very unkind to me when upset about something not getting fixed on her timeline. I have fears about going into another legal contract with her (fear that she'd sue my socks off if something went wrong in the future, God forbid), BUT she's a very interested buyer, and we could possibly do FSBO and save the commissions. I haven't asked for a CMA from my realtor, because I'd feel bad if I had her do that, then did FSBO. Ideally I'd like to get $50k-$60k out of it, but I don't know if the market would bear that price. Any tips on how to gauge the price? Zillow has been grossly inaccurate at estimates in the past, due to the nuances of it being in an oil boom/bust town. Redfin is not in this area. And Trulia doesn't give much helpful info either.

Any wisdom to impart on me regarding this? Would you use a realtor for both transactions? I haven't even mentioned our interest in selling to tenant in property #2. Tenant in property #1 was planning on moving out in the next few months, when her lease is up, and I told her today we are going to be putting it on the market. Because of a legal issue we had when purchasing property #1, I need to dot my I's and cross my T's, so I will be using a realtor. I also don't have a built in buyer for property #1 like I do with #2. 

Thoughts?