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.
Honestly I think the pan, mask and the glasses are kind of a curse? How would I ever know if people actually like ME or just the glasses? All of my relationships would require keeping the glasses on, that's just stressful! How would I enjoy the taste of food or ever try new meals if it's always great? I'd just make the same thing over and over while being content, not actually happy. And if I sleep only an hour a day that's just gonna put me out of sync with the world and lead to loneliness.
The long cool down on the penny is honestly it's best feature, gives you room to still live your life.
This is something I've thought about for a long while. As a socially awkward kid, I read the stories of King Arthur. One of the stories about one of his knights (can't remember which) the knight is given an enchanted item that charms everyone he speaks to and makes them like him. This immediately captured my fascination as a socially inept kid, but the more I thought about it, it would be living hell.
You would never EVER believe anyone genuinely enjoyed your company again, constantly wondering if it was the enchantment. Even if you removed the item and found someone who liked you natrually without it, normal appreciation or regard would NEVER come close to the enchanted one, and it would now FEEL like they disliked you. It would poison your entire life