When I set my watch, is it okay to roll the time backwards?
As a general practice, no for mechanical watches, yes with some limitations for quartz watches. For some watches with mechanical movements, this is a bad idea for several reasons. First, the mechanisms are usually designed around moving forward, so some cannot take the stress of reversing properly. Second, after a mechanical watch settles in, reversing the watch against the pattern of wear may cause unnecessary additional wear.
Both mechanical and quartz watches with dates and other complications handled by mechanical parts can be harmed by rolling the time backwards -- especially near midnight.
Despite that, many modern watches can be reversed with no problem. But it is best to check with the manufacturer to be sure. The one general rule is that if your mechanical watch's second hand does not stop when you put the watch in time setting mode, then you should definitely not turn the hands backwards.