Social lubrication, helping people get laid since 1785
I think there's a good chance this meet will happen in the next two months (tops) with some good planning 
When does everyone have time off? I am off from Feb 26 (earliest to leave) to Mar 9 (latest to return). We need to find common time off and plan some event at least, IMO. Anyways--I think flying down on Friday afternoon (so to arrive Friday night) and then meeting that night, then having say Saturday for some winter sports (someone would need to look into the cost of rentals) followed by meeting downtown, and then flying out Sunday afternoon would be the "common" route for many of us that have school or work. It would give us maximum time to meet up, hang out, see the area, and then get back. The lowest I see, though, is $290/person for such a scenario, not including the cost of transportation. That's with all of us staying in the same room (2 doubles and a cot?).
I think we also need to consider a touristy/airport hub with a attending member of our community. Sort of setup 1/2 nights where we "crash" there, or something similar. Obviously this won't work that well if they have many roommates, but I guess that's still the standing problem with HLP USA--we're such a big nation that we don't all have the luxury of jumping in a car for an hour or two and meeting up.