I appreciate all the different responses! To answer some questions, if I were to sell, I'd end up buying another place to rent out. I'd kept an eye on what people are saying are good places such as Worcester, Roxbury, Everett, Brockton... kind of all over the map but all places that seem to be good buys right now with potential for appreciation. I don't want to count just on appreciation though, I also need cash flow.
I've thought about going for a triple decker in one of those areas, I know those are what everyone has their eyes on though so I don't know how hard/easy one would be to get. I have not talked to any lenders yet, however last time I asked my bank about it they said I would qualify for a very low downpayment mortgage in the future due to my status with them.
However I also agree that Medford could really continue moving up, and I don't want to miss out on potential continued jump in prices. A lot of people I know are now looking to buy in Medford and are already complaining that the prices are high... I remember this same thing happening with Somerville, except Medford does not exactly have the "cool" factor (yet?) which Somerville has. The condo fee is very low which is good.