There are plenty of fish in the sea so my strategy is to not go after these properties when there are many others without the hindrances. 

There are plenty of deals all day long in the oceans we fish in.

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)?

You seem to be fishing for other people to let you play with their money. 

He lived in Alameda CA which is a small island next to Oakland and pretty expensive these days.. he invited me to lunch so he could give me the keys to the gates so i could ride my quads on his ranch and fish in his lake.. 

Because he said "learning how to fish, is better than not knowing how to catch food at all."

The market is NUTS

But as talking to contractors and engineers I believe this route is to big of a fish for me to get my feet wet for this being my first ever true real estate investment.

The trick is to find a contractor that over time you buiild a relationship with and can trust so when he tells you the actual job is going to be $15k you know with 100% certainty he has your best interest at heart and isnt just fishing for more work than is actually needed.WIth this being your first deal, OBVIOUSLY you are not going to have that relationship with any one contractor yet.