Gotcha. Yeah I saw those -> indicators right after sending you that question. I just installed tree locally -- it is nice! I keep forgetting about that one. I'm gonna take all this as inspiration and come up with a better system. I currently have a server/desktop with my whole entire data archive and a laptop that will have some backup-worthy files, I'd like to be able to easily back them both up locally and to the cloud.

I think getting better organized like you did first is the right move. I have a system in place for the desktop machine that works fairly well, but buying this new laptop threw a wrench into that system because I'd like to reuse it in both contexts but it's currently not equipped to do that. I'll figure it out :) But like you said, being organized helps efforts like that (among many others!)