[BadBadJellyBean]

You are betting that whatever you host doesn't live as long as the upgrade cycle because it'll probably be a pain when the upgrades finally arrive. I'd rather have smaller version jumps more often than a huge jump with everything changing after a long time.

[andix]

It usually doesn't live until the end of the support cycle. And if it does I will probably migrate it to a fresh VM instead of upgrading the distribution.

[BadBadJellyBean]

I'm not worried about upgrading. I'm worried about the whole environment being potentially several versions newer than the old one. All shared libraries. All services. Everything new. And now you have to make a software that has had little upgrades run on that. Have fun.

[6031769]

Completely agree. A fresh install beats an in-place major version upgrade every time. Less hazardous and gives an easy path to clear out all the accumulated crud.