If I was going to shift to a more cross-platform system, I wouldn’t want to use iCloud. Too specific to the iOS/Mac OS ecosystem. Besides, I don’t really trust iCloud that much. I’d rather use Dropbox for that sort of workflow (which I mostly do at the moment anyway).
I really want to simplify as much as possible and that means keeping everything in one system, ideally. In practice that is still a bit difficult to do. Evernote is the closest I’ve been able to come to doing that.
Maybe I’m just too hooked on the impermanence of everything. In fact, that is almost certainly what this is all about.