The building was mixed-use with parking which was a rare find.

Could you handle it if the HOA decides to bump the HOA fees next year or hit you with a $3,000 special assessment to pave the parking lot and replace the roof?

Most of the routine payments and receipts are handled by auto pay.

This property is a cabin, but doesn't qualify for traditional lending, as it's a sort of tiny home /park model built on a chassis, however we would own the lot.The current owner states 2019 rents were about $10k (via VRBO, AirBnB, etc).

Those investors may be able to structure a "rent-to-own" deal for her or you whereas the home is "purchased" (loan released), moved (to a mobile home park?)

Its a quaint old town that had this nice little creek , they never had a problem until the suburbs expanded and all the roads and parking lots . 

Indoor mailboxes, package lockers (Amazon hub), dog parks, pools, playgrounds, storage garages,etc.

Be sure to talk to the city about allowed uses in the zone, as well as parking requirements. 

I think with the offer of off street parking, or even the garage+washer/dryer I can get more.

I bought a 4 unit myself in Rogers Park/Edgewater boarder and new bars/coffee shops are popping up all over.