@Knight:
….it so it took me quite a while to have a working system again...).
What should take time :
Ones its up, you create a backup 'disk' (CD, USB stick, etc) so when your principal media dies (SSH, Hard disk etc) you can reboot 'in a snap'.
Ones in a while, when you're up and running, and you modify your pfSense config, store it also in a save place - better yet : write it to your backup media …. ;)
You do can all this while "all is good and you have plenty of time".
Btw : you should only do this if the "internet access" is important for you. I do understand you have other things to do (as we all) ;D
Now, the update day arrives.
Now, you are ready !
Without even thinking, you hit that upgrade button.
If things go downhill afterwards, well, you reboot from your backup media ..... and you're up. I assure you that you have a workable solution in 5 minutes, whatever the outcome will be : new version, or boot to old version.
Added to that : something I don't do - but, which I should do :
I'm running pfSense a a vanilla ancient Dell Office Desktop PC" (stripped down - I removed everything not needed on a firewall.
What I should do : every time pfSense includes a new freeBSD kernel (meaning : new drivers etc) I install FIRST the original new FreeBSD OS.
If that goes well, I'll have a pretty good that pfSense works also.
Easier will be : run pfSense on pfSense certified machines .....