Is there ever going to be a problem if I don’t upgrade to wordpress 2.8 or whatever?

I’m on 2.7 or whatever was current a few months ago. Now it’s all like "you should upgrade to 2.8" but I have a whole bunch of WP sites and I don’t want to upgrade them all cuz I’m worried something might get goofed up.

it’s 99% going to just be security patches, you might be prone to getting hacked

I had a few plug-ins fuck up when I went to 2.8.

I usually update the plug-ins before I update wordpress

new update now. Just updated one of mine and found out simple tags won’t work with 2.9 yet

I usually wait a few weeks to a month or so, after wordpress releases their update to update mine

wut? Login to your dashboard

but usually wordpress has issues with plug-ins or other things with every update released, so I try to wait to see if they get it all worked out before I update

Not to be retired but how do I find out if things are worked out or not?

I usually wait awhile… but then again, I have so many WP based sites I would kill myself if I updated every single one on every single update.