Carefully read the update notes, don't click them away. If breaking changes don't apply for your system, you can update.
Then always update to the most version of any software as soon as possible. The only reason to temporarily not update is if the new version has a known issue that prevents proper operation for you. Sooner or later you simply have to update, and the more intermediate versions you skip, the more work is to do. Newer versions have bugs fixed, so issues you might have and invested much time to work around might simply have been gone with newer versions.
There is just one reason to not immediately update OBS: if you have a plugin that's known to not work properly with the newer OBS. As far as I know, all the 30+ versions of OBS don't contain plugin breaking changes, or the plugin authors already updated their plugins, so it's safe to say this is no reason to not update.
The one major change in OBS 31 that might break things is the new code signing certificate, which is solely relevant for anti cheat systems for fps games. You saw the many crash reports after OBS 31 release? As far as I remember, these were due to this change, and this was just from fps gamers who tried to stream some specific shooter game that didn't update their anticheat in advance. The anti cheat checks the code signing certificate to identify it's OBS and not some cheat that's trying to interact with the game, and since these checks are hardcoded, a new certificate requires an update of the game anti cheat.
If you don't capture fps games with anti cheat, this isn't relevant for you and you can just update. If you do capture fps games with anti cheat, check the specific game if it updated so far, and the majority of them did update in the meantime, so this is also no reason to not update.
Ok, the other major change that might break things is that Nvenc in Nvidia Kepler GPU (GTX 600+GTX 700) isn't supported any more. This is an easy check: does your machine is that old? In this case, don't update and consider a hardware upgrade since that hardware is quite obsolete these days.