In your case, it might make sense to track flight deals from BWI as well then.

If you get Columbus Day or Veteran's Day off, those would be good weekends to start with. Airfares are generally cheaper. Labor Day and Memorial day are doable but tougher. MLK and President's Day make for nice escapes from the winter cold, but I've found tickets to the Carribean are astronomically high.

I would also figure out accommodation options early. For me, getting a cheap fare is half the battle. There's a bunch of destinations that I've up put on hold for the moment because they don't have cheap hotels (in $ or points).