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If you get your mail from a mailbox across the street then you will have to wait for the cover of darkness.
Suppose you live in an apartment building with all if the nail boxes down on the first floor. What hour would checking the box be reasonably safe?
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Indeed! This does make the level of risk somewhat variable. It very much depends on country of residence as well.
For example, in the US, typically mailboxes are right on the street, so that mail carriers can simply stop their (right-hand drive) mail truck and deposit mail without needing to get out. In the UK, most mail is dropped through mail slots in the front door if I'm not mistaken. In other places a box is attached to the wall beside the door on the porch.
My current situation is a neighborhood of discrete houses, yet all the mail boxes are gathered together in one central location, so it'd definitely take some strategizing to check the mail without getting caught! (Especially since a county Sheriff's Deputy lives in the house right across the street from the mailboxes! D: )
My last residence was an apartment building with the mailboxes on the first floor at either side of the building, so also very risky! It was the kind of place that's very affordable, and in a decent area so... people tended to come and go at all hours, with jobs with all sorts of shifts. Still, I did check my mail naked in that building a few times, and usually found around 3-4 AM to be the best time... before the early risers get going, but after the late night folks get home.
But you're right; you'd need to account for that in your planning stages for this dare.
Alternatively, you could use a service like UPS. They have drop boxes for small packages and envelopes in many cities in the US, and I imagine other delivery services do the same. In the US, at least, they cannot access mail boxes (it's a federal crime to do so), so they typically deliver packages right to your front porch.
For an added thrill, you could mail it requiring an in-person signature so you have no choice but to answer the door naked to your UPS driver. Well... if they bother to actually enforce that requirement, which in my experience is something like a 20% chance, lol.