Should I own where I live before investing in other properties

[Michael Mahan]

I live in a suburban area of Massachusetts where the cost of buying a house is high but rentals are cheap compared to living in Boston. We commute into the city. I am looking to begin reinvesting in rentals. I moved out of my condo and rented it out when I moved to this location with my girlfriend. Then sold it a few years later when the market took off. Now I'm debating buying a condo (average 300k) in the area I am currently living and buying rental in a slightly lower income part of MA. My ask is -should I continue to rent and buy rentals in a different area or should I get my own house in order (pun intended) then branch out into investment.