It's not the general requesting of ride reports that gets annoying, or requesting on check-in. When I'm talking to 20 planes and giving ride reports every couple of transmissions (referencing a fix that almost everyone is flying over on their flight plan), then someone who's been on frequency for the last 5-10 minutes asks, I'm likely to start getting snappy. Usually, when the rides are bad, especially if there are only one or two good altitudes, my workload is pretty high. Everyone is cris-crossing each other, and they all want the same altitude. Meanwhile, everyone is asking about the rides as they check in, which takes time to give everyone the report. If the rides are bad, expecially if you hear me chattering seemingly nonstop, listen up! If I say moderate turbulence all altitudes between FL320 and FL380, that means ALL altitudes in there. The other problem with situations like this is spacing. One day last summer, the only good altitudes in my sector were FL260 and FL380. In addition to all of the requests for ride reports, everyone was at (or trying to get to) one of those two altitudes, and we were doing miles-in-trail spacing to numerous airports on crossing routes. The speeds quickly became a major issue, as I'm sure you can imagine, increasing my workload even further. Now, I'm not complaining, because I love my job. Dealing with this situation is part of what makes my job so much fun, but in the moment when I'm dealing with a situation like that, I'm so hyperfocused I can get snappy much quicker and easier than I normally would (and I've been told I am way too nice a controller).
That being said, when I'm riding in the back, I really want the pilots to get the smoothest ride possible, and I don't care so much about if they are annoying the controllers! I hate to admit it, but it's true. I try to remember this when I start to get upset with pilots, but sometimes, in the moment, I do forget.