Talk to local agents and investors and see where in the area a househack may make sense (won't be easy to find around Boston, be prepared for that). 

Your sister could be added on as a non-equity employee and issued a W-2 salary for services provided. 

@John Moran,There are number of active investors as well as service providers who are frequent contributors on this forum.

Everyone can handle a deal that goes 100% your way 100% of the time but you should be prepared to handle things should they go south on you as well. 

A property management company is a vendor and I wouldn't give equity in exchange for vendor services. 

So the only question is, does the Market Rent for that location and Type of Unit cover the HOA, plus Debt Service, plus whatever other Expenses need to be paid..Because if it doesn't, the Landlord is in for a world of hurt!.

But taking my willingness to move on as weakness and incrementally increasing the bill amount unreasonably.So, I want to prepare myself for all eventualities.

@Matt GilroySo he's going to know that something is up when you show up and start inspecting in the corners.Do your inspection, mark off your checklist, and prepare for inevitable personality conflicts over nothing as the relationship shifts.Showing up is one of the basic rules of self-managing your rentals, Matt.

After a certain point you should be prepared to go without mentors and most learning will come through experience, but if you want to cut down the learning curve and accelerate your path to your goals find someone who has been there before and learn as much as possible.

Although I would primarily be in the business of wholesaling I’m also going to have my real estate license and I want to offer the services of listing homes and helping people find their dream homes or investment properties.