I decided to get my license primarily to represent myself in my investment pursuits and to eventually work with buyer/seller clients once I get acclimated.  

You would have to be careful since you are a real estate agent that you don't take a commission or represent her. 

I will be in town next week/the week after and will begin poking and prodding my city representative and see if I can get an answer out of them.

I'm not bashing realtors...I'm still a licensed broker in Texas but no longer represent buyers/sellers, I only sell my investment properties.

The other thought I had was to purchase a large home that has a separate living space (in Cali they call them multi gen suites) and do it as an off market so I represent both sides of the transaction.

I represent a builder that builds off market multiunits (4-plexes).

I think its great that this site represents both sides of the landlord coin.. its not all RA RA RA OR financial freedom so many talk about but not sure they know what that really is … I think they know the concept but the reality of doing that through rental properties is probably not exactly what they envision .. 

Luckily for you, I represent a brokerage in GA, FL, NY, and MA where I can locate properties on your behalf utilizing the local MLS service. our team matches opportunities to you based upon your criteria and only send matches in price, preferable return rate, school district, select neighborhoods, etc. that you've selected in advance.

I know you’re in Massachusetts, however, if I were to represent myself would that then mean they need to have a realtor?

Or just return to one person as the "appointed representative".