Upgrading the distro can be a pain and this is true for all Linux distros. As with the updates, the longer you wait the bigger the changes are between versions. For a recent example, I just did an in place upgrade most of my RPis to Raspbian buster. They are mostly running the same stuff with minor differences, all are headless.
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1 I didn’t upgrade because it’s remote and will require a 100 mile drive to fix it if something goes wrong, that one will stay on stretch until I make the drive for other reasons.
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2 completed the upgrade without any problems and are now happily running buster
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2 failed in the middle of the upgrade and I had to rebuild the SD cards from scratch, which wasn’t that big of a deal because all the set is scripted. I didn’t go this route in the first place because I was too lazy to go and physically remove the SD cards and burn the new OS onto them in the first place.
As you can see, it’s not all that easy of a process.
So you will probably want to make sure you have everything backed up and start fresh with the new distro, installing the OS and then reinstalling the software and restoring the backups of your data. You have a couple years to think about it and maybe start setting up your backups and recovery needed to accomplish this.