The fatigue mask makes the underwear irrelevant. If I have an extra 7 hours in a day, I can spend some of that showering. You'd essentially gain an extra 3.5 months every year in additional time, plus you'd never be tired for any of it. There's a lot I could do with that time.

The Pan is questionably useful. Delicious food is cool, but has limited use with the cooldown. If I wanted to start a restaurant or something, could I only cook 3 delicious meals in a day? Or does "while in use" mean I could use it to continuously cook for 8 hours? If so, you could run a 3 star Michelin restaurant.

The shoes also seem limited to me. I can only use it until my stamina runs out? My stamina is already so low that 5x isn't even that much. I suppose I could use them to win the Olympics without training, but would they count as a violation? I really don't want to get involved in the underground track and field ring.

The glasses are very useful, lots of ways to find success if you know your way around networking. Being able to talk your way into or out of anything could get you crazy money, power, success, etc. in whatever you choose to do.

The penny is also mad useful. It essentially covers the abilities of all other items, albeit with a massive cooldown. Even still having an entire day of things going your way 26 times a year is an insane amount. You could win the lottery, start and sell successful businesses, find the love of your life, whatever, as long as you can make it happen in 12 hours.

I think it really comes down to the mask, the glasses or the penny. The mask really appeals to the tired part of me, but it doesn't really give you any superhuman abilities, just extra time to be normal, and I'd probably just waste it anyway. And while the glasses would be useful daily, you'd still have to do a lot of work to get yourself into important social situations to make use of it. Essentially your job would become networking. With the penny, I really think I could use its power to get myself into those situations by sheer luck, and then also have them go my way, by luck. I think I could end up making as much progress in those 12 hours as I could with 2 weeks of the glasses. Plus with the money I win from the lottery, I could fund projects faster instead of having to talk my way into funding.

I'm gonna go with the penny.