Hey @Jonathan Guerrero, welcome to BP! You'll find some excellent information and people here so you've come to the right place. My advice would be to start reading as many as the blogs and forum topics that speak to what you're looking to do, listen to the podcasts, and get out there and meet all other people who have done what you're looking to accomplish.
In 2016 I started out with my first multi family purchase, did a good size reno using the 203k, and will be trying to acquire the next investment property later this Summer. There are many benefits to owner occupying a multi family property. Tenants will be paying the bulk of your mortgage payments, you'll build equity via principal paydown and appreciation, more tax benefits of owning vs renting, and you'll be living very subsidized and able to save that much more cash to roll into your next investment property.
My advice would be to zero in on what area you'd like to live. If you work in Boston, try staying somewhere outside the city with easy access to subway system (Malden, Melrose, Quincy, Braintree, etc.) and if the prices are too high and outside your comfort zone, start looking at areas with easy access to a commuter rail stop - this will give you a larger geographic option to consider.
If I can help answer any questions you have in further detail, please don't hesitate to reach out via direct message. I'm happy to share what I can!
-DJ Richmond