I've even moved all hist stuff out of the area, and barricaded that unused entry way (plywood and nails), and posted no trespassing signs, only to have him tear it all down and move back in before the next morning.My biz partner gave the police an earful, and they said they'd patrol the area more frequently (stop by whenever they're around), but I'm not too confident that anything will be done.So, I'm brainstorming for some options.

One thing with Condos and Town Homes is the repairs are usually less frequent.

I am always watching rents in the area though, frequently looking at trulia/padmapper/apartments.com/zumper/craigslist ads and snap a photo of every "for rent" sign I see to call up and find out.There is a lot more variation than simply how many bedrooms a place has and where in the city it is located in, property condition, layout, density, and the environment around it factors into the price a lot, and rentometer doesn't give you much insight into that.

He is experienced and frequently has access to off market deals.

The only constraint is that I'd like to see this replicated more frequently so that more of my extended family can take advantage of it and receive benefit out of it (both on the investment front as well as on the home ownership front). 

I am hoping that I don't need to repurchase the same list frequently to renew it.

I try to match the lease term, frequently 10-30 years, with the loan term.

So he will be frequently in the new place but when it is rented out with airbnb he will stay at his other apt. 

Frequently, vacation rental rules differ if the residence is "owner occupied" remember depending on the state "owner occupied" can be as little as 2 weeks out of the year.

(Apologies for the late reply, I don't frequently browse forums..