Ambitious and educated in Massachusetts

[Duncan Banks]

My name is Duncan Banks, I am a 30 year old military veteran with a BA and Master's in architecture. I have been, so far, disappointed with the work and pay that I have been able to command with my education in this market. I have often fantasized about climbing the real estate ladder from the ground up through sweat, dedication and tenacity. I am excellent with my hands and have a limited background in construction that I accrued while in school. I am currently working 40hrs a week at an architectural firm on the south shore that provides a steady paycheck. I am a true beginner when it comes to real estate but am hoping to absorb some of the expertise available on this site before buying my first property.
My ideal goals are to acquire a live in duplex that I could restore the side I was living in while renting the other. When one side was completed I would move in to the other side and repeat the process. The idea of maintaining properties to rent has always been appealing despite the headaches of being a landlord. I would of course sell if the market was extremely profitable for sellers but paying the mortgage with rent would allow me to wait for the ideal time. I would hope to repeat this process several times with multi family units. I welcome any advise, criticism, or helpful links that I should read before starting this process. Thank you all in advance.

Duncan