Midwestern markets are pretty popular so I would find a good agents that can connect with the right members of your core-4 team. 

I have also managed the day-to-day operations which involved me ensuring all amenities were stocked, coordination with the cleaning staff, and handling communication with challenging guests.My Remote work skills have proven me to be a great asset for my property owner who was not much involved in running their airbnb rental but was well-informed by me. 

I’ll need an accountant in my “core-4” to help me lower that... more like “core-5” now...

If you really want to go down that path, I suggest that you apply to work for a syndicator or RE Private Equity shop as an analyst or operator for a year or two, and browse through 100+ deals over that time period, underwriting each one, and trying to figure out, over that time, which ones you were "right" about, and which ones you were "wrong" about, as best you can.

With an Operating Agreement, separate bank account, etc.? 

Both of those neighborhood (all of City of Boston in fact) would need for you to be an owner occupied operator, are you planning on moving to NE?

Let me address some of your questions about operating this type of setup.

400+ flips, nearly a billion in transactions and over 4K units under management, experience/operations in 27 states, 5 countries, 3 continents.....

This duplex is in a short term rental are that I currently operate in.

Angela Harding TPM Realty  Sorry my english not good I from ukraine, what it means "rent a broker's" Rent a brokers mate is when the officer of your company is a licensed broker so you can legally operate.$1,000 per violation and per day if you manage properties without a broker.I know if folks managing thousands illegally in Toledo.If only I was a whistle blower hehe10% fee from the total fine isn't a bad pay day, right...?