It shouldn't be a gamble - that's why there are permitted tolerances - If you do the sampling right then the accumulative error isn't bad - you wait 1.5 bit times (or the hardware waits 1.5 bit times for you) after the start of the start bit then sample every 1-bit time after that, so creeping errors ought to be fine - but yes, there is less wiggle room the faster you go.
I hate to disagree with you, Gordon, but this isn't strictly the case. If your baud rate generator is wrong (as is often the case with an AVR on an internal clock) then the creeping error is always there and always in the same proportion.
Assuming the most common 8-n-1 format, you have ten bits including the start bit. Hardware detects the falling edge of the start bit and waits half a bit period; if it's still low, then it assumes a valid start. It then repeatedly waits one bit period to sample the next bit; the final sample is the stop bit which should be high.
If you have a rate difference between the two ends, then the sample time gets closer and closer to a transition; if the receiver is faster then towards the eighth bit instead of the stop bit and past the end of the stop bit if the sender is faster. At a >5% differential then the last sample is of the wrong bit - and its worse if the receiver does best-of-three filtering, as many do, since that shaves the permissible timing difference.
This is apparently worse if you have a fast baud rate because with most clock/baud rate combinations (if you're using a non-baud-rate-generator clock) you have small non-integer divisors for the clock and the error is proportionally greater. So it's worse because you're starting with an incorrect baud rate to begin with.
But for accurate and reliable async communications, you need accurate baud rate generators. They _must_ be within 2.5% of a standard baud rate, or if you're using non-standard rates at each end, withing 5% of each other.
Neil (pedantic mode = off)
(of course, there are encodings like biphase mark which are much more robust and don't give a hoot about baud rates, but I don't know of any hardware that encodes them; you need to roll your own.)