Agree here, cloning disks on linux haven't worked for me in 20 years, particularly doing anything like raid, encryption, or lvm. Start over and just get a base os working.
OS is fairly irrelevant outside of sysctl's and services loading from etc, but meshing between major revisions or distributions here is problematic at best. Clean build is best.
I've imported my homedir's lock stock and barrel across versions and distributions, to some varying success over the years, but I always run into weirdness that leads me to largely blow out my home directory in doing so too. If I nuke my system to go to another, I largely manually rebuild it each time. I also try to re-document anything new, as invariably I'm doing something with new hardware, mobo, secure-boot, and just general distro weirdness, so it's often worthwhile to do so for next time, or at least some good start to remembering what I did to make something work.
Again, clean is best. Chrome has profile imports, most messaging means too, rest I'm not adverse to rebuilding from logins to things I need. I get weird issues across even google profile imports, but it's much harder to nuke that and start over, sadly enough.
Ubuntu hasn't upgraded cleanly for me between any revision since 10.04, so I just presume I'm rebuilding it during an upgrade one way or another, and often end up doing some major mods due to ubuntu blowing up an upgrade horribly. I tend to now look at it as an opportunity for improvement procedurally, but manual rebuilds afford me some "do-overs" I do not discourage...
Why I run Arch now with rolling upgrades - I've not had to "start over" in years now, even with major kernel, graphics, and DE changes. Ubuntu on my XPS has been a general disaster since upgrading from 16.04 on it which worked mostly, then going 18.04, even upgrading to 18.10 it's still a basketcase. Wayland replacement seems mostly the root cause. Feels like when they shat Unity upon the public randomly.
My goal is to get arch working on the xps too. So far, I haven't had such luck sadly, so still stuck with ubuntu for it at least for now.
-mb