Re: Upgrading can be painful?
I've never found upgrading painful. I did come late to the party only starting with Mint 13 (the first with Mate as default), and have been upgrading in place ever since without problems. I'm sure as soon as the option appears to go from 19.3 to 20, that will be smooth too.
My Raspberry Pi 4 running a Raspbian Buster image that started off as Wheezy on a 256MB Pi B, and has been run on every variant since and upgraded in place for each release along the way.
I do make sure I have backups before I start though!