Hey, there are expenses involved!
As an aside, I would suggest that several of you steer clear of any competitions that involve following instructions in an OP.
mmm
I just thought of another one. Using only a pair of chopsticks, I can transfer 10 ordinary glass marbles from one bowl to another, switch the chopsticks to the other hand, transfer the marbles back to the original bowl, and repeat the whole thing, all in less than 60 seconds. I actually won a contest for exactly this entirely useless skill. The contest was actually just to move the marbles from one bowl to the other in 60 seconds, but after I had finished with that task right handed, I switched to my left hand and moved them back. I had something like 32 seconds left, so I did it all again. I think I won a free soda or something.
Crocheting lace. Lots of people can do a granny square or a simple zig zag afghan, but very few have my skill level. Even though the stitches are the same, it’s not easy to get the tension right and keep track of how everything fits together in the more complicated designs. And I can do it with thread and 1-3mm hooks.
Doing calendar math in my head. It’s a pretty useless skill now that you can pull a phone out of your pocket and find out in just a few seconds what day of the week June 13, 2077 will fall on, but take away the electronics and I can beat 99 random people in providing with speed and accuracy the day of the week of any date between 1901 and 2099.
But I would want at least half the boodle. Screw that $1000: to paraphrase Rocky Rococo, I’ll do this for you for five thousand dollars.
It’s the “give mmm $9000” game!
I can write a sonnet better than 99 randos.
Hosting a hospitality suite for conventions. Tell me what you want, tell me what you want to spend, tell me how many people and what the theme of the convention is and tell me what hours you want it up and running…and stand back. What will it cost you, besides the bill for supplies?
Nothing except a room to sleep in, because I do things like this for joy, and I have been doing things like this since the mid '80s. There is a small group of people that can do what I do, but the ones that want to do it just to make people happy are very few and far between.
The game is obviously asymmetric, given that we’re choosing the contest, not any of the 99 randos. So why assume that they’re paying the same amount that we are?
I can wiggle my ears better than anybody I’ve ever met, but I’m not sure how it can be measurable. Speed? The ability to alternate ears?
Regardless, I think I win.
Write a publishable novel.
My chess rating has been over 2200 ELO for decades. 
Of course I would prefer to be the next chap with this skill:
Chess.com says I’m in the 97.2% in rapid, and considering most people don’t play chess I imagine I’m into the 99th percentile there. Looking at the site I play tetris on I don’t see any percentiles, but I think in 40L sprint I’m also likely 99%. Been a while since I took a standardized test, but I’d be reasonably comfortable on the GRE I think.
That’s very impressive!
Ummm… can you use chopsticks to transfer food from a dish to your mouth? Just wondering…
Typesetting.
Operate a stat camera.
Paste-up.
Proofreading.
All very valuable skills nowadays.
I can bake the puffiest, lightest, flakiest buttermilk biscuits you ever saw. I wasn’t always able to do this; since retiring I’ve been able to put my mind to it and perform all the little steps and tricks that are necessary for the best outcome.
I can also make killer pie crust, just by eyeballing the ingredients; I never measure.
Cross my eyes and move them one eye, left-and-right, at a time.
Tripler
Oh, I’m a hoot at tennis matches.
Funny you should ask. I can pick stuff up with chopsticks left handed just fine, but putting that stuff in my mouth is hard. For some reason, my left wrist isn’t as flexible as my right to make that final move!
I think I’d stand a good chance at beating 99 random people at a round of disc (frisbee) golf.
Darts. I would often crush large numbers of actual dart players, so against random folks, I figure that’s money in the bank!
And using this same logic, I think I very may well add Mogul Skiing and Desert Motorcycle racing to the list. There are many, many better than I. But it’s likely that in a Blind Draw of 99 people across the world that none of them have ever done either and aren’t going to learn in a day!
If they are truly “random people”, then they would need to be picked at random. That is, they wouldn’t be just the people willing to spend $100 to try to beat the other 99 at a specific task. They would just be 99 people pulled at random who wouldn’t even know what the contest is for. If it is a contest like that, then it probably would pay out pretty well if you could pick your own task for $100. You’d likely win over 99 randos who agreed to try the task without even knowing what the task was.
If on the other hand it is 99 other people who are willing to pay $100 to try to beat 99 others at a defined task, then likely you would end up with 99 people who think they are pretty good at that task. For instance, if the task is juggling, anyone who is not a juggler won’t do it. They’re not going to throw away $100 on a task that they know they’re going to lose at. On the other hand, a professional juggler might consider it because they would figure there’s a realistic chance that they could beat the 99 other jugglers who decided to do it.