The friend that has a spot now runs a coffee shop out of a trailer and will occasionally go to events and such on weekends.As far as permitting...where the property is located, we are out of city limits.

We bought this home mainly for our family to enjoy and also occasionally rented it out as a STR.

Occasionally you will see spec homes on infill lots in our market with basic builder grade finishes and they just don't sell well. 

Hopefully you have reserves that will allow you to overcome the occasional hiccups that will inevitably arise. 

I think you can learn plenty from reading books, listening to podcasts, following forums, and occasionally buying a cheap, less than $100, course.

I'll add a couple more to the mix: the erosion of trust due to dishonest or deceptive practices, accounting errors with an owner's funds, exorbitant mark-ups on maintenance, poorly handled repair situations, extended turnover times between tenancies, and occasionally, just downright traumatic experiences linked to the previous management.

I work at a Wayfair call center and receive the occasional call from people buying furniture for their rentals or others who need door knobs and pulls for houses they are building and selling.Over the past month or two I have been receiving significantly more phone calls from people who are furnishing condos to rent.

I will occasionally get left holding the bag but in the long run I should come out ahead.  

My tenants occasionally will post their maintenance requests there too.

Though I totally understand the desire for privacy I have found that aside from the occasional shared kitchen use, most independent roommate situations rarely result in folks looking to hang out in the common areas.