I see. In that case you should really try tmux; I didn’t vibe with screen either but I find tmux quite usable.
For the most part I just open several terminal windows/tabs on my local machine and remote with each one to the server, and I use tmux only when I explicitly need to keep something running. Since that’s usually just one thing I can use like two tmux commands and don’t need anything else.
Oh and for stuff like copying and such I’d use rsync instead of primitive cp so that in case it gets interrupted I only copy what’s needed.
I wouldn’t bother with virtualization and such; you’d only complicate things for yourself. Try to keep it simple but do it properly: learn some command line basics and you’ll see that in a year it’ll become second nature.