in reply to
Writing/Debugging locally and then uploading
It sounds like you're on the right track, though changing operating systems is inevitably going to add some difficulties here and there. But I do roughly the same thing.
The key to make it work for me was to arrange the scripts, templates and modules so that everything was under one root directory that I could upload via rsync. That way I didn't mistakenly upload some pieces and not others and loose time debugging that kind of problem.
If the site you are building is live, I'd suggest uploading to some kind of staging area, then cutting over to the live site after a quick test. Changing environments often reveals things that even diligent local testing won't find.