[striker101]

1. Million dollars but every other week, you have to dress up like the opposite sex. You don't have to go out in public but your bound to go outside since it's every other week.
Yes. There's plenty of women's clothes out there that could pass pretty easily for men's clothing nowadays.

2. Million dollars but every time you use a washroom that's not in your house, you have to put a butt plug in your ass until you go to sleep.
Yes. A bit inconvenient, but I rarely use public bathrooms anyway. The occasions that I do, would definitely be worth it for a million dollars.

3. Million dollars but every time you spend money, you have to take off a piece of clothing. You can only put back on clothes when you get back home.
Yes. Traveling abroad would be a challenge... Shopping online would make a lot of it easier, and pre-ordering/buying as much as possible in advance.

4. Million dollars but every time you wake up, you have to go to the bathroom and piss on yourself in the bathtub. You have to then jack off to a edge and then you are able to do your normal routine.
Yes. It'd be annoying, and pretty gross. But I shower first thing in the morning everyday, so at least it'd be cleaned up right away. I feel like a million dollars would be worth the hassle.

5. Million dollars but everyday, you have to ask a random stranger if you can drink their pee. if they say yes, you have to drink their pee.
Probably. I'd mostly count on the vast majority of people saying no. That seems like a pretty safe bet. Even if 1% of people said yes (which honestly seems like a very generous estimate), that's not that much piss drinking in exchange for a hell of a lot of money. Pretty sure that'd be enough to make up for the embarrassment of having to ask that as well (also helps that I'd be asking strangers, so not as much worry about committing social suicide).