Should we invest in multifamily in Malden MA?

[Connie H.]

We bought a multifamily property in Watertown MA last year.  It was a good decision.

If you live in Greater Boston area and pay attention to multifamily investment, you would agree with me that 2017 has seen an average of $50-100K rise in the price of multifamilies in this area - i.e. Watertown, Medford and Somerville.  

I have two questions to ask for your kind input.

1. We have a small condo apartment in rural Boston. We had to pay about $50K of cash for it due to updating requirements forced through by its HOA a few years ago. The market price for it now is unfortunately the same as when we bought it 10 years ago, around $210K.

Should we sell it next year and claim that loss now, or should we hold it for 2-3 more years?

It is currently rent at $1300/month, but the cash flow is still negative considering the mortgage and HOA fees. We get about $6000 worth of value every year counting the principal that is paid. If we sell it, we will claim that $50K loss immediately, but we can get about $100K back and we can use it for MF investment in area closer to Boston.

2. Which one is better - To invest in two families in Medford or Watertown (Somerville has totally priced us out and we cannot afford three families anymore), or to invest in a potential 3 families in Malden? My husband thinks that Malden is traditionally considered a rundown area to live for young professionals. For the prior two towns, we probably will not have any cash flow.

Flipping house or converting multifamilies to condos are not something we can do. We both have full time jobs.

Thanks for your input. We really appreciate it.