WO party thoughts:
If everyone is getting to the location city under their own steam, $1K for a weekend event based around a decent venue would be simple enough to pull off. It could be a venue / hotel with one big night 'in' but in any decent city, there wouldn't necessarily be the need (or obligation) to all stay over in one place.
A dinner, a celebration involving some organised moments and entertainment for the big night, sure.
But also a get together in advance / meet and greet excuse ahead of it (the day/evening before maybe, once everyne's in town), plus a day's optional events after the big night. If the third day events are (say) 'supercar driving' or 'helicopter races', then sure, it would be more costly than (say) a bar and a band, or go-kart racing, but the suggestions could be found with consensus and be optional for those who want to pay to take part, while not a cost to come along and watch with a beer. There would be little point in not socialising, but it needn't be embarrassingly forced, just things to allow relaxed mingling, laid on at key points.
One formal, fancy and structured evening with 'befores and afters' that are up to whoever fancies them can work to build a great weekend around.
I'd reckon since everyone is different, a central and classy / very cool thing can be agreed as a base point, then add-ons can be fun extras that you can enjoy or skip or choose an alternative to. Every town has it's appeals for exploring, and adventures to seek accordigng to taste - so some time that is unstructured is a good idea.
If a bunch fancy the beach, or the casino on the afternoon after for a little recovery, why not? Then a meet up later for a bite and a few more beers somewhere relaxed (and again booked) for a bit of a VIP feel would be a nice way to catch up with everyone again.... And maybe round the weekend off with people who have met at last, or stay on and send time with new (old) friends, if you fancy it.
Whatever it is, it must be memorable; something to never forget, something fun you know if you told them back home what you'd done for the weekend they'd be jealous. But.... also it would be your reward for all the sitting in front of a screen for countless hours, someting you always hoped that one day you'd feel was finally paying you back, big time. Something that is worth treating yourself to.... And sharing with some of the people you been through it with.
Excuse the ramble - but what d'you reckon:
A little freedom and a little classy structured stuff - options for wild or chilled... according to need / mood / budget?
Edited a little - I am still thinking..!
EDIT 2: Jeez - party plans on hold?!!!