You sound like a person who values the work he’s done and doesn’t want to lose it. Maybe i can help with that by relating some of my experiences in that area, since it’s also important to me.
When i first came to linux the distro that i landed on was Ubuntu 11.10. That was… i think it was the last version that came with the gnome-2 panel setup, or maybe the first one that made Unity the default.
Anyway at that time, maybe 5 years ago now, there was a utility that a guy (Tony somebody?) had written, and what it did was inhale your working partition and spit out an iso file. I forget the name of it, but i used it for a year or two.
The problem with using an iso file as your primary system backup is that then you have to boot into it before you can restore from it by installing from it, and basically you end up waiting a lot while files are copied and restored.
And the really bad thing about that, in addition to being slow, is how are you gonna be sure it’s a valid backup if you don’t restore from it?
For various reasons i decided that using an iso might be okay for distributing a copy of your system, but not so great for backups. So i built a utility called partitionBackup, which is basically a text-mode-fullscreen interface that makes it convenient to create rsync commands, and perform actual backups, without having to remember a lot of syntax and figure out whether you want to back up /sda4 or /sda14 or whatever.
So what i keep on a usb stick carried in my pocket (which has become a microSD card over time) is bootable into several distros that i’m working with ATM, and which also contains a copy of all my working data. I find that this works way better than trying to generate an iso image, and is a lot less hassle.
Dunno if that information helps or not. I’m willing to share what i’ve built, but it’s written in PHP-5 and relies on ncurses.so to perform its fullscreen text mode schtick, and i haven’t found a way of getting ncurses installed with the PHP-7 that is in the repository. As a result, i’m still booting into debian-jessie to perform backups, which is something i’ll need to deal with somehow.
Good luck, hth.