However, I currently have a job as a waiter, and I know that even if my investments go according to plan, they will not bear enough fruit in the short term for me to quit my job.

We should break ground in about 3-4 weeks so I’m looking forward to seeing some fruits from my labor.

Having a small taste of the fruits from your hard work and sacrifice will turn you into a success addict and accomplishing your goals will become your crack. 

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)?

Essentially meaning that any time of work you put in, be it in lead generation, submitting offers, etc, you won't see the fruits of those labors until about 90 days out.

The market is NUTS

You need to be hyper local - I'd go to brokerages and hand out sweets (or fruit!)

I work heavily with investors and honestly, 70% never buy and do waste our time, however that is the nature of being an agent..doing what others won't because most of the 18,000+ licensed agents (just in Central FL.) are looking for the low hanging fruit and right now, there is plenty of that. 

I think the lowest hanging fruit would be the popcorn ceilings.