Best Direction for Beginner House Hacking (Boston 25yr old)

[Kyle Washburn]

Hey BiggerPockets, this is my first post here so bear with me. I've been educating myself on real estate for the past few months reading and listening to podcasts, and have decided that my biggest goal for 2021 is to buy my first investment property. Before getting into my main question, here is some background on me. 

I'm a 25 year old living in the Boston area. I started my own business in college and ran that for 3 years before closing down and getting into SaaS sales. I will clear just over $100k for 2020 and have been living below my means while also investing (side business, BTC, the market). I am locked in to my current lease until August 31st, and plan to close on my first property before August 1st. Currently paying $1120/month and would prefer to own the property and collect from tenants rather than being the tenant! I am planning to have $30-$40k cash ready to invest. Ideally, I'd like to be cashflow positive in this first property while also living for free myself. Now, onto my thoughts/questions.

The Boston area is very expensive, and I can't get a decent multi family for less than 600k or so. I have been looking in the Lowell and Worcester areas for cheaper units that would allow me to get in with a lower down payment and leave some room for improvements. I work in Cambridge and all of my friends/social life is in the Boston area, but I'm willing to sacrifice to purchase my first place and house hack in a different area (Lowell/Worcester). I guess my question to you guys is, would you recommend I start out with a home under $500k in the Lowell/Worcester area, live there for a year or two, and then move out and try for my second property? Or do you think it makes sense to look in the greater Boston area for a more expensive property that might have more appreciation over time/is closer to my work and social life? Again, willing to sacrifice location for a great investment.

I'm trying to get started on this process early and appreciate any tips, advice, and or recommendations from anyone who started out house hacking. Also happy to answer any additional questions you may have. Thank you all in advanced!