I lamed out and did a prop for 500. You could make one and it could be anything. We made a 500 placard with my boobs making the two zeros. If you did make a 1000th update prop you could take a couple of photos with it in every shoot between now and then. Especially useful if you shoot with some other charms. When the time comes, put together a collection of images. You could also take your prop on the road and get a bunch of flashing photos in different locations.

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Some things I considered but ended up not doing:
1. Collecting little video snippets from other charms saying happy xxxTH update. You can paste them together and included them in your update. I would do one for you and I imagine a lot of the charms active on this board would as well.
2. Dominoes, you could set up "1000" dominoes and then knock them over with your nipples or something like that. Make it a video update.
3. 1000 lashes? I like to be flogged but even 500 seemed like a lot to fit into a video update and make interesting.
4. Money. I thought about doing $500 (100 five dollar bills and who would really be counting anyway) You could tape some together and make a skirt, top, etc.
5. Fake Cake - pop out of a cake decorated for happy 1000th update.
6. Exercise - I was considering putting together a routine of exercises that would add up to 500 repetitions. You don't really have to do them all and you could make fun of yourself cheating. So, 100 jumping jacks, 100 squats, etc. adding up to 1000. You can strip as you go or do it circuit style where you do a few of each and then take something off and go again. Maybe by the end you're drinking a beer and your photographer is finishing your workout.