@Kendrick Prinston You'll want to rethink the short term rental angle if you're in Boston. They just dropped the hammer on that market with a slew of regulations designed to stifle that market.
My advice for most people is to look south of the city. Norfolk, Plymouth and Bristol counties much more affordable than most towns inside RT 128.
The first thing to square away though is your financing. If you find a property you want to buy, you will need a strong pre-approval from a lender or proof-of-funds. Nobody will accept an offer if they don't know whether you can actually buy it.
That's especially important around here because anything that's a reasonable deal will go under contract very quickly. You won't have time to start the pre-approval process in time to save a deal that you find today.
@Kendrick Prinston , hi! Agree with Charlie on short term in Boston - new regs make that less feasible in Boston proper - but I work with folks who have robust portfolios of short term rentals in Malden and Chelsea, with the transit access of Boston but fewer limitations. Still feasible!
Same goes for wholesaling here - unless you're in trades, hard to get good numbers on quick turnaround in Boston proper, but with some access to capital, more feasible in Malden, Chelsea, Everett, or in Dorchester, West Roxbury, even Norwood.
I know we connected off-forum also - happy to chat more if it helps!