Factors like these will show the level of confidence people have in buy and hold real estate in your 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 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)?

In other words is the sale price of the relinquished property the only factor determining how much title ‘investor A’ needs to take vs how much money each will bring to the table?

How much a particular lender will loan to you will typical depend on a multitude of factors including DTI, Income, the property, etc.  

What other factors would you consider?

And this does not even factor in the last few deals we closed for our clients!

There are a million factors here. 

Definitely, have only one kitchenThe second meter is a factor if you are attempting to represent a portion of the property as an ADU.

BTW, we love this market because we've got a major university a few blocks away, Fortune 500 employers in the area and other factors which drive constant rental demand.