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Allow everyone to choose their time windows, but require at least 24 hours span between the two time window changes.

are you a frontend engineer? cause I'd hope the time checking happens on the server ;-)

What about using vpns to connect through different timezones ?

Where is the server getting information about the user's timezone from pray tell?

It doesn't matter if it's being checked on the client or the server. If the user controls what your code sees, they can fake it.

The user can choose their time zone when they sign up, and the service can prevent them from changing it (or heavily limit how often it can be changed)

It doesn't matter if they fake it. They're only getting one window per 24 hours.

Problem: user goes on vacation three time zones west of their usual location, and now they can’t access the site tomorrow.

Worth it.

Have seen this happening too often when my sister, brother, or wife were using the iPhone time limit for apps.

The sibling comments are a perfect demonstration why projects tend to balloon in complexity and ever-increasing requirements just to deal with rare corner cases.

YAGNI. A niche tool whose selling feature is time-restricted usage shouldn't have to account for weirdos that miss the point of it and cheat with their clock.