If you're fine with upgrading only every few years with Windows, you should be fine doing the same with Ubuntu - so just stick with the LTS and you'll have less problems. Also avoid adding third-party repositories, they can really break stuff if they replace key packages.

Considering the UI it's mostly a habit thing, personally I've never used Windows on my own computer for about 15 years and it's really a pain for me to use it each time I have to.