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"A commenter mentioned using Dropbox for synchronization as well, which seems attractive, but I’m not sure how clean that would be on headless Linux servers." Dropbox does work pretty nicely on headless Linux servers, you just have a daemon running constantly with none of the GUI extensions. I use it for keeping some code in check.

Nice list of things to try, I don't use vim but I've been putting off doing 3 of them (caps remap, iTerm and zsh).

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For some (entirely irrational, I'm sure) reason, the idea of constant and automatic deployment of my dotfiles across all my boxes gives me the shivers. I like that extra bit of control I get from doing it with a git repo.

Same, which is why I git repo them as well. It's mostly a nice way to keep a few bits of code in check, plus handy for quick private repos without needing all the nice stuff from GitHub/BitBucket.

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