Optimal intro investment strategy - Boston area

[Evan Leibovitz]

Would greatly appreciate some advice and venture this may help many other folks currently on the sidelines of this challenging market.

Basics:

-I currently live, and wish to continue living, in Boston/Cambridge/Somerville/Charlestown in a “nice” 1-2 bed (w/ significant other)

-Assume I am fully extended with 20% down on a ~$900k property (or less on more, as I am willing to tolerate a negative cash flow of ~$2k/mo, inclusive of my personal rent)

-I do not presently have a contractor/“team” and am not personally “handy” thus would need to factor in significant costs to any rehab

Options, as I see them:

-Buy a 1-2 bed in an area I want to live, live there

-Buy a multi family in an area I want to live and rent the other unit(s) - may overextend myself and I will not be able to carry the nut if significant vacancies

-Buy a cash flowing rental property (single family, multi family, condo) in an area I don’t want to live (e.g., Everett, Revere, Chelsea, Dorchester, other B/C neighborhoods, out of state) and rent in my desired area

If you were in my shoes, what might you do (aside from compromising on my desired location and house hacking a MF in a B/C neighborhood)?

Thank you!