1) I would cash out the property. By your own admission, you are pretty much treading water on that investment. Yes, in 20 years, it will be nice, but do you actually plan on using it? Do you plan on moving back? I would want to know more about your renters, but if they aren't stable/long-term/safe, I would bail on this property. I love owning property, but I don't like being an absent landlord. It can lead to bad things. I am familiar with the Boston Real Estate Market and understand demand is high, but how long would you want to float without a renter. Economically, you could do it for a few months, but it would definitely hurt.

2) I like the mix. Keep contributing the max

3) I would take 5k and take some risky bets that are LONG. My prime example would be Greece. This is a country that has people running, but realistically, you are young enough to wait them out. This place is not going to disappear off the map. I think the quote is when others are greedy, be fearful and when others are fearful, be greedy. Well, right now is a prime time to capitalize on that sentiment. You have the age and free cash.

3b) Since I am taking a risky bet on one thing, I would be a lot safer with my other money. I would take the other 5K and invest in Utilities like FTR, SALM, T, VZ. These high dividend stocks that are reliant on pre-existing infrastructure and high-demand necessities are good bets on the long-term.

SALM - Full Disclosure: I have a lot riding on this. I don't agree with their views, but I highly believe in money. There are, at my last count, 10 Republican Presidential candidates, and this will not be the final count. All of them will be spending big money on radio and television ads. This doesn't take into account all the SuperPACs and smaller races that are going on.