Hi Will!
Welcome to the Boston area! My first multi was in Melrose - I was lucky to get into that market in 2010 when things were a bit down.
It is great to hear that you have prioritized being debt free and getting the funds together for your first investment. Being a first time home buyer is very difficult because you feel the pressure of trying to get the best deal. I know it took me 6 months to find my first investment and my agent at the time was super frustrated with me. Worse is that I am an architect and I see all the little details of each house - it drove her crazy.
I left architecture to flip houses and sell real estate. After some successful flips I just opened my own real estate company and I am loving the life!
My word of advice is - don't expect your first deal to check every box you have. Prioritize what is important to you and try to build realistic expectations for what you can get out of a house hack. What towns are specifically looking in? Two towns right next to each other could be worlds apart as far as investments go.
I wish you the best of luck!