Richard - VE7CVS
I understand Jeremy's position about upgrades completely - I work for a company that has been known to take 18 months to perform the regression testing necessary to release a new version of a C compiler to the developers!
(Yes, we do value our customers!)
Unless I'm actively helping someone test software (which I will certainly be happy to do once I get time to dive in to the UDRC!), I generally don't do 'apt-get upgrade' very often on my servers or workstation. I've been bitten by conflicts, where packages maintained by different groups aren't fully in sync in the repository - and by packages that I've had to build from source, where it becomes necessary to do lengthy rebuilds to get things back in sync. For stuff that I use regularly my motto is - "if it ain't broke, don't fix it!".
Raspberry Pis are cheap enough - and, especially, SD cards are really cheap - so I don't mind taking the plunge with my experimental gear, I can clean up quickly if it fails. (Pop in the previous SD card - done!) My Ubuntu desktop machine - not as much. My MythTV server - rarely!
Keep the distribution files on hand - if you try something that results in 'unparliamentary language' :-), worst case is to reload the card from your distribution and try again.
If dealing with upgrades bothers you - you don't have to upgrade until something breaks, but realise that you may have more work ahead of you because of the amount of change that has occurred since your last upgrade. It's a tradeoff.
- Richard, VE7CVS