The sleep mask looks like the obvious bet. Have you ever been awake for 20 hours straight? It's not debilitating, but after about 18 I start getting woozy. I'm gonna go with it anyway, because even if I take the penny and win the lottery, the one thing money can't buy is time
Au conteaire, money well spent does, in fact, buy time. If you are broke and have to spend half your day riding buses to get your errands done and you buy a car and can get them done in an hour or two, that is half a day you just bought. If you can hire a maid and a chef, that is all of the time that would have been spent cleaning and cooking that you now get to figure out how to spend. Don't let anyone lie to you that money cannot buy time, because being able to use money to speed up tasks or offload them entirely is literally buying time.
Yeah the penny is crazy OP. Ultimately, if something can be done, you can do it. Ignoring what you said for a moment, which is entirely true.
Get rich, create company that is focused on sleep research and ways to reduce/eliminate it while staying 100% healthy, unlimited funds, top minds, and every month you can help speed things up significantly.
And if it's fundamentally impossible, you'll still have plenty of other goals to choose from, and you'll absolutely appreciate having the entire day free to do what you want while having to sleep, vs having to still go to work but sitting up all night.
The other catch is, while it states a cool down of 20 hours, functionally you'd generally have to be awake 23 hours, unless you had the luxury of being able to sleep at any time. Sleeping every 20 hours for 1 hour isn't going to stay at a consistent time.