The buyers did a long inspection, multiple days... made a huge request for concessions based on what we knew to be purely made-up issues.

At first, he was anxious about having multiple tenants under one roof, but with the right house rules spelled out up front, it turned into a solid monthly cash fow for him.

Listing on multiple platforms does affect ranking by platforms but not as much as you think.  

Quote from @Tod DuBois: Hostaway appears to integrate with the multiple channels - but I hate to do a software setup and learn it's not a good place to do what I need to get done (which is work as little as possible and optimize my occupancy).

I've done multiple BRRRRs myself and tend to find the best opportunities in C, C+, and B- neighborhoods where the inventory of distressed homes is still there. 

I personally have no connections with anyone who is involved in this niche and I'm wondering how other people have started their journey.

This property would have multiple income streams, including as an airbnb, wedding venue, bed and breakfast, corporate retreat. 

Because you gotta have multiple exit strategies. 

The majority of our expertise comes from experience and having a specific book of real-estate clients who are involved in a wide variety of activities.

These structures are significantly more complicated than a typical 1031 Exchange structure and there are inherent risks involved in the transaction, some of which are discussed below.