Freash install or Upgrade and Clean

I’m currently running HA in Docker on a Ubuntu 18.04 host which in turn is a VM on a ESXi host.
I’m a few version behind and I have a number of ‘things’ that I’ve added over the years that either didn’t work as expected, needed extra tweak time that I never got around to doing, or broke and I never figured the solution out.

So do I start over with a fresh build and migrate the working bits over and then go live or do I patch things up with my current install?

I’m leaning towards a fresh install and perhaps Hassio? I ran into issues very early on in Hassio’s life and switched to core. Advatages to using Hassio over Core or Vice Versa?