I was sold on the mask at "the wearer go falls asleep in 30 seconds" then read the rest. Undeniably the best one here.

Sincerely, a night owl who takes forever to fall asleep, and is perpetually tired

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.

The penny for sure. The mask might give you 7 more hours but the penny gives you 8, if you use it for money.

The glasses could be nice, but that depends wholly on the value system. Is charisma naturally rated 1 to 10? +35 is awesome! On a scale from 1 to 1000 not so much.

Glasses.

Look, everyone votes for penny, but really if your social skills are exceptional, rendering you able to "flawlessly navigate social situations", you can get a lot of it anytime.

Want a super high paying job? Glasses! Wanna hit that girl? Glasses! Wanna get anything you want? Stay cool, with the use of glasses!

Penny does seem OP, but only for as long as it's active, and while it is on cooldown (which is, on average, a month) you live your regular life with all the misery, and even if you've managed to accumulate money and influence through your lucky streaks, there's always a lot that can go wrong. Besides, a random nature of a penny means you can never rely on it, and always have to assume you'll lose. Betting on a penny makes you the ultimate RNG person, with dramatic rises and even more dramatic falls. Betting on glasses makes you insanely powerful on demand. Always. Anytime.

As someone who's continuously tired after tanking mono and COVID, I'll take the mask. Heck, I'd even take it if it gave me 8 hours of restful sleep. Just anything to wake up and feel rested for a while

Definitely the underwear. I have the opposite of whatever gene SE Asians have that makes you have no BO. No matter what I do, my BO can defeat any deodorant in ~6h.

I kinda like the skillet. I hate cooking, so can I just throw some chicken breast in there and some vegetables and then come back to a delicious meal?

I know others have loopholes, but using the loopholes ruins the fun.

The shoes are probably worthless to most folks, +400% stamina isn't a whole lot when you only have 1 stamina. Would they work during sex? You're faster, but also last longer?

I'd probably take the mask, just because that's what would benefit me the most right now.

The glasses are OP, everyone's like "the coin bruh"

Nah bruh, you know the power of speeches? Now have it so everyone's on your side all the time. There's no cooldown, it's just always active.

You can just talk your way into anything. You don't need money if you don't have to pay for anything, if you want money you can still talk your way into having it. You wanna be president? Why not! Etc etc. The glasses are unreasonable.

The frying pan, mask and coin are definitely the best 3, in order. The frying pan is good for QOL, and if "while in use" is for an unlimited time, you could definitely start a business with it, as it would most likely make supernaturally good food. The mask just straight up effectively make your life longer because youd be concious for more of it. The average lifespan is 75 years in first world countries, so assuming 8hrs of sleep a day, most people will sleep for 8212 days in their lives (~22yrs) however, assuming you got the mask at 18, and only slept using it thereafter,by the time you are 75 you'd only have slept for 2470 days(~6.7yrs), meaning you are concious for 24905 days, which is almost the same as having lived to 115 with normal 8hr sleep. However, the coin is objectively best. The only real drawback to the coin is the 2 week wait period, which seems would be triggered regardless if you land a tails.that being said, a 50% to be capable of limited reality bending for 12 hours every 2 weeks is still super fucking good. You could just try to do something thats physically impossible and it should work anyways. The capabilities are actually almost limitless with it.

Penny. I like to live dangerously.

Charisma glasses would open up all kinds of awful things in the wrong hands. And there will be hell to pay if you take them off at the wrong moment.

The shoes open up a whole can of worms. Just consume the last two decades of Flash (DC comics) media and you'll understand. Breaking physics like this opens up all kinds of utility, but the universe does not abide by people ignoring thermodynamics and spacetime.

The sleep mask sounds like a way to get anywhere from 5-8 more wakeful hours in a day, every day. But do I also get tired like normal if I use it? Because if I have to go to sleep every 20 hours, and spend 2-3 of those hours absolutely exhausted, that's gonna completely screw up my schedule.

The frying pan is my speed. Get people over to your place and you won't need the other items. Just make awesome relationships and build a posse around impossibly good home cooked meals. Win everybody over, work your way up in society, and start slinging tasty meals at state dinners. Together, you'll conquer the world one plate at a time.

Edit: The coin is a monkey's paw in disguise. Stay away.

Edit2: Underwear... look, if you need this, you have to re-evaluate some stuff. Otherwise, healthy body odor is kind of a factor in courtship. Plus it says "odor free", so that includes perfume. That said, if you're the rugged outdoor type and want to trek Patagonia for weeks on end, this is the item to pack.

Frying pan is the obvious choice, I'll invade Mordor with it.

This is a really cool list since it gets a bunch of people in the comments to fight over which one is the best. Obviously several could somehow let you gain a million dollars, but money alone might not be the limit.

BRB figuring out how to do an item dupe glitch for infinite lucky pennies, then making a macro that flips 100 of them in 2 seconds.

Lets just balace the penny by saying it makes you 100x more likely to succeed.