I was doing STR in both Boston and Cape Cod and Boston/Cambridge did their best to kill Airbnb, The Cape tries to embrace them, though some backlash from Boston created state requirements to them.

Welcome to BP - I think you should definitely embrace the idea of investing out of state sooner rather than later, especially since you mentioned cash flow as your goals. 

My greatest concerns are how to find the right mentor and learn enough to avoid common pitfalls.RE seems high friction to me, iliquid compared to other asset classes with which I'm more familiar but I want to embrace the opportunity to understand how others who succeed with it operate and hopefully give back along the way.William

Stories like nicks make me so excited for life and really allow me to embrace the suck in a sense and grow and turn my downfalls or shortcomings into my superpowers if yopu will. 

By staying informed, seeking guidance from reputable sources, and embracing a patient and disciplined approach, new investors can navigate the complexities of real estate investing with greater competence and confidence.

Now, none of this is the case for an OOS investor who is using a PM who likely is adding extra management fees on top of each repair because ... well because they can.After years of doing this, I know which tenants to avoid and which to embrace. 

By old school, I mean does not embrace or use new technology, is not flexible with shorter minimum stays, operates in the off season (for very seasonal markets).  

Someone said it a LONG time ago, that "an ounce of prevention is worth more than a pound of cure" - yet as a society we have yet to embrace it.I won't dive too deeply into the fact that Big Pharm and the gov't would rather have you take a pill (with its 20 side effects) for pain instead of something like cannabis, and that's why it's still illegal.3.

At that point then embrace "caveat emptor" and go it alone, but until then get someone like Wes Petersen with Stratton Group. 

You can embrace all the face-to-face meet-ups, get to know brokers on a personal level, learn the area firsthand, and get your feet wet close to the action.