Your answer would be it depends on a million things.Like the specific property, its condition, location to desirable areas, local STR regulations etc.We would need much more detail to be able to help.

My hope is to begin building my portfolio (probably fix/flips) this year while I continue to work with local investors on helping them build theirs.

Here some of my advice first Educate yourself Understand the local rental market trends, property values, and rental demand.

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Talk to a local lender to know what you can afford.  2.Research how to do real estate transactions, get a good RE lawyer or find a good investment knowledgeable agent.

That region will require some risk mitigation, and would be better suited for a local flipper specializing in those types of properties vs buy and hold OOS IMO. 

I'd definitely double check and triple check your local/city regulations in regards to rentals, so there are no surprises as to what you can do legally. 

Definitely want to consult with a local realtor or real estate attorney 

I don't have any local meetups but there are a lot of online groups.

Although I have knowledge and experience in my local market, I am most interested in some out-of-state options as I like those opportunities better than what I have locally but know little about where to begin evaluating those markets and the pros and cons of the different states.