Single Family House Hacking in Middlesex/Essex counties

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Hello everyone! I just finished reading Craig Curelop's "The House Hacking Strategy" book. My fiance and I are looking to buy our first house and are really intrigued by the idea of house hacking. 

We are thinking of buying a single family home (ideally in Haverhill, Ayer, Methuen, or Chelmsford, though our budget is <$450k so that last one might be out of reach), renting out a room or two while we live there to help with mortgage, and then moving to a new home in 2 or so years. Ideally we would keep the property and rent out all the rooms once we leave. 

We are completely new to real estate and would love to hear if anyone has done this and what the experience has been like! How has the experience gone? Were there any pitfalls or things you wish you knew beforehand? Also, we are most unclear about the transition to the next home - how do we buy our second house and avoid getting stuck in the first one? That may be a question for our lender, but open to any advice here. 

Any guidance is appreciated. Thank you!

I love seeing people consider house hacking , especially in the New England market

wahat great way to build equity , learn a few things and set yourself up for the next property.

Respect to the hardy willing to step back and jump forward with this process