When will it be safe to update to 6?

I used Update Manager to upgrade one machine from 5.0 to 5.5 to 6.0 and another from 5.5 to 6.0 today.

No issues.

Except that Banshee isn't compatible with 6.0. :(

Just to let you know, I was running Trisquel 5.5 and upgraded to 6.0 and had several issues.

First for some reason, the upgrade didn't complete properly and I needed to run "sudo dpkg --configure -a" to complete the configuration after the reboot(it almost always did that to me with ubuntu too on this machine in the past years, but not on my upgrade from trisquel 5.0 to 5.5). This didn't work at first because for some reason, /sbin and /usr/sbin were not in the PATH variable so I added those to the path before it could execute.

I also had the problem of the bottom task bar being gray. "rm ~/.config/dconf/user" solved that problem as mentioned elsewhere in the forum. I have a dual monitor setup, so I needed to bring the task bar back on the right screen where it was before the upgrade.

I had two keyboard layouts for french and english and my french layout disappeared. I had to reconfigure it. It also trashed my background.

I also no longer had any title bars on any windows. Switching from compiz to metacity solved that partially.

Aside from those points the rest seems to work fine.

It might be worth waiting a short while for things to stabilize, but I'm quite happy with the way things went. I solved everything in the same evening. I remember having a much harder time a few years back with ubuntu when it was less mature.

Hope this helps you to decide whether to upgrade or not,
Cheers!

I upgraded two systems recently. One is a headless home server and test bed of sorts. The other is my personal laptop. For the home server I used do-release-upgrade. It worked without a hitch. The server came back up normally after the upgrade. The laptop also had no problems whatsoever with booting. I couldn't upgrade from the Update Manager however, so I used do-release-upgrade on there as well. As far as I can tell, it is safe.

Upgrade from 4 to 6 via "do-release upgrade -d" on 2 machines terminated with a python minimal error so I just installed from scratch. On another 5.5 machine running net install with Xfce this command led to a successful upgrade.