Advise needed on selling Boston condo and investing on triplex

[Matthew Fermino]

I’m looking for some advice on whether I should sell my condo I rent in Boston and use the equity to get into my first duplex or triplex out of the area.

When I first purchased my condo about 8 years ago I didn’t really have a strategy but I thought buying it, living in it and then eventually renting it for a little cash flow would be the plan. In the last six months or so I’ve really gotten into BiggerPockets and I’m looking to be much more aggressive with my real estate investments. Below are some details and areas of uncertainly

Right now I cash flow about $100 a month which I thought was more until I really did the BiggerPockets calculator and realized my true costs. But I have accrued tremendous equity and could probably clear on a sale about 175k to 200K after fees BUT before capital gains. The challenge is the tax implications I would have make me wonder if I should sell and leverage the equity or hold this and start looking for other ways to build up my portfolio with my “true plan” in place. I’d like to start with some duplex rentals to buy rent and hold for 4-5yrs to build equity then sell and keep up leveling my net worth.

I really appreciate any advice and would love to connect with some like-minded folks in and around Boston/Providence