I am wondering how pain-free is it to and upgrade from stable to stable. What I found with other distros is things would break with every single version update. having switched to debian stable I find it much more stable, not a single crash so far.

While i can add loads of other programs (not from official repos) and make it less stable, how easy is it to keep debian going long term by mostly installing from the stable repos?

My assumption is due to its long deevlopment and bug fixing cycle it should be relatively pain free (maybe a couple of packages that need updating here and there, but nothing major), correct?

If you only use the official Debian repositories upgrading is as pain-free as it can be, if you follow the upgrade-procedure described in the release notes. Of course you will have to look for changes in configuration files that you have to make possibly, when a newer version of a program uses a different format or different options.
The debian team can't and won't, of course, test the upgrade process with third party repositories, so here it up to you to find out how good that works.

You should also be careful when dist-upgrading to not press <Enter> automatically but look at what may be removed as well as installed. On occasion, due to dependencies, apt may want to remove packages until the dependencies have been updated. This just means that sometimes updates have to be put off until you do not have anything being removed on which you rely.
The above is more of a problem with resting and unstable but I've read a few posts on here about things like less being suggested for removal.

Re config files and check remove. Ah ok, thanks for pointing that out. I am using everything from the repos (except installing cinnamon from mint repos) so it seems that it shouldn't be too bad.
I remember updating from ubuntu release to ubuntu release. Suddenly wifi no longer works , suspend doesnt work, invoking tty1 with ctrl+alt+f1 and switching back somehow crashes the system. I guess i should have made my question clearer, i meant hardware breakage first, then software, i can live with having to re install a few packages, as long as the system is still usable to do so.

I can't really comment on the hardware. Back in the days when I used Debian on my desktop/laptops I used Debian Unstable mixed with Experimental, so I don't know how a stable-to-stable upgrade would work on such systems. Nowadays I use Debian only on my servers (headless, maintenance via SSH), on those machines there wasn't any problem with the upgrade from Squeeze to Wheezy, except that I had to adapt the configuration for Dovecot.

You should probably purge Cinnamon (save your current config files to someplace safe) and just go with the standard Squeeze configuration for Gnome for the short version upgrade period.

This would include commenting out the repo where you got Cinnamon. I hope this was not the Linux Mint repo. I hope it was the Linux Mint Debian Edition repo.

You should then have a lot less chance of screwy version upgrade problems.

Read the documentation on version upgrades carefully keeping in mind your specific installation and make sure you are aware of any possible problems.

Also remember the power of, as root;
run from recovery mode if there is a problem. This will, most of the time, straighten out little glitches.

If you are installed on only 1 partition I would recommend a clean install after backing up all data and installing on / and /home. This will be more robust in the long run.

I've upgraded using dist-upgrade twice, from Lenny to Squeeze and then from Squeeze to Wheezy just a couple of days ago. Both times went swimmingly.

I followed Debian's instructions to back up my home folder and /etc, read the occasional dialogs carefully before I responded to them, and both times did not need the backups. I'm typing on that machine right now.

Here are the upgrade instructions for 32-bit hardware.

I think it was the debian ones - is this the correct repo?

--- SOurces list---
# Install cinnamon, uncomment after install

# deb http://packages.linuxmint.com/ debian main upstream import
--- SOurces list---
No, fortunately everything is split up.

/boot / /home /usr /var /tmp and swap are the partitions i have.

I make backups on a daily basis so whatever goes wrong i can always go back to a good config.

Thanks, i will look into upgrade instructions, it usually helps to read through before killing a perfectly good (albeit old) install :-)

---------- Post added 05-12-13 at 02:50 AM ----------

I think it was the debian ones - is this the correct repo?

--- SOurces list---
# Install cinnamon, uncomment after install

# deb http://packages.linuxmint.com/ debian main upstream import
--- SOurces list---
No, fortunately everything is split up.

/boot / /home /usr /var /tmp and swap are the partitions i have.

I make backups on a daily basis so whatever goes wrong i can always go back to a good config.

Thanks, i will look into upgrade instructions, it usually helps to read through before killing a perfectly good (albeit old) install :-)