To sell or not to sell, that is the question. Medford, MA.

[TD Wolf]

Overview: This is my first post so thanks for hearing me out. I own a two-family in Medford (near Tufts, Davis Sq, Mystic Valley Parkway) and am considering selling soon--or not. Trying to figure that out. The motivation for selling is to generate capital to use on the next investment(s) and to possibly get more space for me and my family. I bought in Somerville in 2009, Medford in 2014, and am now seeing that insane growth trajectory start to bleed over into other towns--and I want to get in ahead of the curve again like in Somerville and Medford.

Background: I bought the house in 2014 and invested about $30k in the past two years while living in one unit and renting the other. It's now worth at least $200k more than we paid (plus we will get back our original investment--i.e. the 20% downpayment). The rental income greatly subsidizes our mortgage payment. If we were to rent both units, we would clear about $2000/month over our mortgage payment. If I sell the place, I need to find somewhere else for me and my family to live...Somewhere with more space perhaps and near a commuter rail? Ideally, I would be able to keep the house, rent it, AND buy another house but that would drain all my savings.

What would you do in this situation? Options:

1) keep living in one unit and renting the other. Pro: Affords us the luxury of having someone else pay for most of our mortgage. Con: our money is "tied up" in the property and we don't have the space we need with a young child.

2) rent both units and collect $2000/month in profit. Pro: steady cash flow. Con: have to drain all savings in order to make the downpayment on another house to move to. Or rent for a while...

3) Take the money and run. Pro: would produce lots of capital to invest in another property or two. Con: be back on the competitive buyer-side of the market.

Any and all advice is welcome! Also, if I can provide any more background, insights, etc that would be helpful, please let me know.