Real estate by definition is speculative for the most part but value usually increases over time all things being equal (Absent cataclysmic events). 

Making relationships and gaining insightful knowledge may be obtained by attending networking and local events.

Beyond the Monthly Management, Placement & Maintenance fees, all other fees in our contract are IF EVENT -> THEN fees.

Therefore, it is important to think beyond the present and evaluate the best option based on foreseeable future events.

Likewise homes in established neighborhoods can have more owner equity and therefore less likely to have foreclosures in the event of a recession.

If you learn the process when you start self managing it, then you know what to expect in the event it happens to you too.  

BiggerPockets has a "Community Events & Local Meet Ups" section on here that is very helpful!

IMPORTANT:--Guest communications, including setting up your automated messages--Price adjustments (key into seasonal pricing and important events in your area)--Listing description and noting amenities--Guest reviews--Learning from experienced hosts with great reviews (you can do this on many social media sites, including the Facebook group, Short Term Rental, Long Term Wealth)UNIMPORTANT:--Watching your Ring Doorbell camera--Obsessing about minute details that other hosts are freaking out about--Being a control freak about ANYTHING related to this business. 

In the event you keep it as a rental, what is his opportunity cost for keeping his equity in your deal for however long you decide to hold it? 

If you are serious about investing in other markets, I would absolutely plan a couple of trips that coincide with local meetups/REIA events for each market.