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 rehabOptions, 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 areaIf 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)?

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 rehabOptions, 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 areaIf 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)?

It's a place where the regulatory environment has created inefficiencies that you can take advantage of in order to get a cash-flowing property, and then you can hold it for a really long time while Silicon Valley does what it does. 

I have read that in an environment of rising rates, this would negatively impact CRE valuation. 

This is not an all inclusive list of the options available, but I hope this helps!

This will give you better leverage in a competitive environment and you can use additional funds to roll into another asset. 

Where have they had success and what seems to be the environment to them?

Downtown environment, 1 block off a college campus.

You might want to separate the market into "type selection" and "environment/neighborhood selection".

That's good that you found a great team around you to tackle this new environment.