I don't really see how you can make any good decision without knowing what the complex is worth in it's current condition? 

Monster court case waiting to happen.  

Masthope had been rumored to be limiting STR, but it seems they are keeping their eye on the fallout after the big court win in Lake Ariel - https://www.timoneyknox.com/reversed-short-term-rental-regul...

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Defending, These fall into a couple of groups, both nasty Eventually you will either face a Due on Sale clause, a seller bankruptcy, a court order in a divorce that affects the property or a fire insurance claim, a slip & fall, very bad tenant, storm damage, and the list goes on.

I agree, with turning the property over you have to make it ready, account for vacancy and go through the courts for an eviction, all of which will cost you.

@Paul Zofsak how will you prove in court that the tree was NOT in good health?

A few other houses (all single family houses) on the same street are on the market for rental and they (including my house) all get grouped and nestled under one cover listing as “units” of an apartment complex.

If required take him to small claims court. 

There are people who have an entire business helping you set up and design a STR relatively quickly (3-7 days) depending on size of home and complexity but you are going to be paying a bit of a premium but you do save on the headache.