I don't use the classpad myself, but you'd really want to take a good look at the documentation / guidebooks etc. that's up for the new software versions and really see if it's worth it.
On one hand, your calculator currently works fine and does what you need it to do - and you've been using it for years as is, so it's probably instinctive to you on how all the functions work by now. It might be worth waiting until after your Further exams, rather than having to possibly relearn / readapt to the calculator.
On the other hand, if there's new features (not just bugfixes for bugs you're probably already coping with) that will make certain things in Further easier for you this year, then it's probably worth putting in the effort to relearn a few things on calculator.
If there's significant bugfixes, then update immediately. Either way, update or not to update, you'd want to read through most of the significant documentation anyway. I wouldn't update without being informed, in the possible case that some of the changes actually hamper how you like to use the calculator.
I'd imagine the updates would be useful, especially if they've fixed the problem that made every Classpad user unable to do a certain question in VCAA 2010 methods exam 2.
I don't really remember what it was, but wasn't that issue due to students trying to use a particular function on the calculator improperly. I'm not sure, but I remember somebody somewhere (probably on this forum) saying something along the lines of that. (I'll see if I can find it, might just be thinking about something different)