Our handyman team of 2 are moving out of state after working with us for almost 18 years to start/continue their real estate investment journey in a more affordable state. 

These are big money plays life changing profits but RISK you bet..

Cities don't play fair when they decide to go after you.One thing I would also suggest you do is look on AirBnB for the specific building you want to buy in. 

Hi Randall-Congratulations on buying a rental property well back in 2020.I am sorry to hear the property is now cashflow negative $200 a month.Your question is should you sell or continue to keep it with the negative cashflow.Depends on your personal goals and if being negative $200 a month plus any unexpected repairs or vacancies is affordable to you, but if you can solve the negative cashflow by turning the property into a furnished mid-term rental, for example, your future self may thank you.To Your Success!

I also understand accounting and legality may play a role.

I never had that come into effect on my single family home purchases since I never wanted to personally be on the hook for such a high mortgage, but I think it might come into play for an MFH. 

The fed's cut will be too late and they will be playing catch up, as defaults and Job Layoffs continue to mount. 

South End’s growth should support that play.

5K rent seems cheap for the area so I would continue with that.

That’s where details come into play.