Other than price, my main care about is the closer which handles the paperwork, communicates with you and the lender, and handles coordinating the closing.

That's how I would handle it as a renter, that's how I would expect my tenants to respond.

What recommendations do you all have for making a deal like this work and finding a team to handle it?

The pros of condo rentals is that you don't have to handle/pay for exterior maintenance or lawn care (outside of your dues). 

DM me and I'll send you their instagram handles if you can't find them.  

If you can handle waiting another 3-6 months, that's what I would recommend.

I figure I could handle a lot of the rehab myself.

I'm sorry to hear this.Contact a local attorney who handles L/T routinely for advice and do what they say.You can likely file an Unlawful Detainer to have her removed.But you might also try contacting her Housing Authority caseworker, posting a notice & attempting to meet with her in person and being extremely empathetic about what she's going through. 

As the new owner, I'm trying to get a handle on the issues so that I can achieve maximum cash flow.

They're going to use their experience in handling all sorts of different situations and try and come up with a solution.