Major cities where STRs have only began rising up and gaining public spotlight with the rise of AirBNB are more likely to have more shifting and less stable regulatory environments since those areas are still in the process of trying to find the balance for STRs within their markets. 

We want to get a few rentals up and running and then (if all works well) begin bringing other friends/investors in to invest with us.

Thanks friends!

Is there a friend, family member, or colleague that has real estate investing experience?

Start with your closest friends and family but they will invest with you because of your relationship not necessarily because of the real estate or your real estate acumen. 

@Kasey Hardt very interesting,  didn't realize this was a pattern but even I've got friends that are getting recruited to the area for medical device startups etc, so could be a very interesting trend to watch.

I think one of the biggest analysis paralysis thoughts is on landlord- or tenant-friendly areas.

Akron is a very blue city and are not very landlord friendly - source of income protections, etc... 

Hey John,I work with several different property managers, which I refer to for my clients (I'm an investor friendly agent over here).

Hello,I am a real estate investor located to Southeast MA, I own and manage a small portfolio of 23 units and am looking to expand and scale out of state as the returns and market have been quite difficult in my area: due to CAP Rates, specific building class I am looking to invest in, and rising interest rates/minimal inventory, as well as it would be nicer to be diversified and in a more landlord friendly state.