I wouldn't unless there's a game you want to play that requires you to update. Right now, all exploits that work on 9.9 have been updated to work on 10.1. It's not likely there will be a new kernel exploit, even then it might work on newer firmware as well. Pretty much, don't needlessly update but don't be afraid to update if you have a reason to, unless you'll lose the ability to use your main exploit. That's how I generally do it.