Probably not a big deal on a $20k gain, but if you hold on to the property for 10 years, payoff the note, capture some appreciation, etc you could reasonably be looking at a $150k gain and the capital gains taxes on that would be significant.Compare that to the cashflow you'd expect to receive over the 10 years - is it enough to wish paying the capital gain taxes?

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)?

A Magistrate would not allow an eviction if the occupant told the court they were than a tenant.I wish there was a way around this too but courts will require a foreclosure even for a property in a trust. 

We wish we had started investing in real estate sooner.

The buyer can either assume the mortgage if the lender agrees, or purchase the property “subject to” the mortgage if the lender isn’t agreeable or if the buyer does not wish to approach the lender or assume liability for the mortgage.

I wish I'd have taken advantage of the opportunities available to me while I was active duty.

I wish you the best of luck in 2022.

Good luck and I wish you the best on your real estate journey!

I wish you the best of luck this year and the following!