For me it was the opposite. I had Ubuntu installed and wanted to do a upgrade to the next release, took around 2 hours "settings things up" where I just said fuck it and force closed it.
My experience with big release distros was like that. I rarely had an upgrade complete without issue. Rolling release has been good to me so far. Granted, this was 10 years ago and things gave probably gotten better since.
I like EndeavourOS (Arch based) and OpenSUSE Tumbleweed (or Gecko Linux). But if you prefer sticking with apt based distro Debian Sid is a rolling release.
I used Manjaro in 2015 for about a year before switching to Arch and sticking with that for a long time. Recently I tried EndeavorOS for a few months, then I switched to Void just to try it.
I think so, but from what I hear it is pretty stable, enough to use. I'd keep backups of important files, but I do that anyway. I use the Branched release myself, but an aquaintance of mine uses rawhide.