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Some of the stuff I run is pretty ancient. I should upgrade. But then things usually break.

Why do things need to be so complicated?
As it is written in th Holy Book:
"If it has to be broken then it have been had to be broken." and "Thou shalt break first to have something to fix." ;-)
I upgraded two squeeze and one lenny this month. It went rather smooth; lot of config-fixing though. #Debian handled library deps just lovely.
Now #Debian upgrades I'm not afraid of. Those go smooth far more often than not. (Though... lenny? Jeez, that's ancient!)

It's just that I'm running stuff like postgres 9.6, and the last time I tried upgrading (dumpall -> upgrade -> restore), everything broke, error messages were completely unhelpful, and I ran out of time. So I'm back at 9.6, and feel a little bad about that.

Guess I'll try again a year or two from now. :P
I have two kinds of pg upgrade: for small db I just let `pg_upgradecluster` to do it and so far no trouble. For big ones I use `pg_upgrade ... --link ...` and have backups ready [no trouble so far 9->13]. 😛
Hmm, hmm. I should try that. Maybe I will, I do have a couple of very small DBs to test it on.

Thanks!
On that note, my little instance is using ~19gb Postgres, and 36gb+ on media storage. Not sure I want to imagine how big a larger instance is.
my matrix db is about 110 GB. I'm strengthening my soul for a month now. :-]