South Boston Property - Sell or Hold?

[Jeff Neblett]

Hi all,

I am looking for some advice related to my first property which is a condo located in South Boston, MA that I purchased a little over two years ago. My girlfriend and I currently live in the condo. The market has really appreciated and I am considering my options for the near/long term... I have two primary options I am considering:

1. Live in the condo until my girlfriend and I can find another property (preferably two units, one of which we can rent out) , make some minor updates and rent the property for the long term.

2. Live in the condo until my girlfriend and I can find another property (preferably two units, one of which we can rent out) , make some minor updates and sell the property within three years of moving in order to take advantage of exclusion of tax on capital gains for a primary residence. Hopefully use the equity to purchase my next investment or two.

Any thoughts? My gut is telling me to hold the property for the long run, take advantage of some cash flow and principle pay down and possibly use a home equity loan for additional investments in the future. Losing out on the capital gain tax break is quite significant though...

Thanks!