House Hack in Boston/Cambridge urban area using STR?

[Rohan Thakker]

Hoping to get some thoughts on my house hack strategy and see if someone has similar stories or tips to share from the Massachusetts area.

I initially started my search with a multifamily strategy in mind in a slightly more suburban parts like Malden, Dorchestor area and doing a LTR on the additional unit but soon realized that I am not ready to make the suburban transition just yet. So trying to rethink the strategy and buy a 2 or 3 bedroom SFH or a condo (if I find a rare HOA that allows STRs) within Boston/Cambridge urban areas and doing a short term rental in additional rooms.