)Rollouts are conducted in phases. Typically they start at 1% of devices for around 24 - 48 hours; we watch the return rates and resulting device checkins and error reports (if any), and make sure nothing looks wrong before sending it to more. Then typically it goes to 25%, 50%, 100% over the course of a week or two.
What the percentages mean is that when your device checks in, it has a 1% chance (for example) of being offered the OTA. If it doesn't (randomly) get an offer, it will never get an offer until the next batch.
IOW, once your device checks in and gets turned down, that's it until the next batch. Mashing on the "check for updates" button just causes your device to check in again, and get automatically turned down again. Think about how that makes your device feel! WON'T SOMEONE PLEASE THINK OF THE PHONES?!
That said, once the new batch does start, hitting that button does give you a new roll of the dice -- but once. Since devices usually only check in for system updates every 24 hours (I think? Certainly on a many-hours basis) this can get you your shot sooner than it would happen on its own.
So, mash away.
Edit: also, keep in mind that this isn't first-come/first-served. You're not racing other devices to get your slot in the current batch, or something.
. Chances are a developer will post the OTA update file before your device is selected for the update process anyway, so those who still want it as soon as possible can still get it that way. 
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