I've got a fairly unique setup, and work on a Windows machine that runs my Ubuntu VM with KDE(where I do all development).

I take monthly snapshots of the VM, and carry it around on all my computers. It drifts from time to time, and I just end up just overwriting it with an older version when I fumble with some settings. Once every 3-4 years I do a clean reinstall of the VM.

I tweak a bit frequently used software like PyCharm, but aim to keep everything in stock and updated constantly.

I've not had any issues or regrets in the last 5 years and I'll carry this on indefinitely.