Is there a "learn you a vim" or "poignant guide to vim" out there? Because the handful of times I tried vi/vim I got some stuff done, but didn't really grok it.
This goes for Emacs, too. I get the feeling I've never really used these tools the way they're meant to be used.
The best way to start with Vim is the included 'vimtutor' command, which opens up a document that guides you through basic editing operations (on itself).
After that, being around other Vim users (in person, on the vim-users mailing list, or subscribing to the !vim group on identi.ca, etc.) is best - being able to ask someone "Is there a better way to do X?" or have someone watching over your shoulder say "I can't believe you're doing that the slow way!" is a great way to learn.
The best long-term solution, I've found, is to remember that laziness is one of the great Programmer Virtues, and pay attention whenever some editing task gets tedious, and take a moment to look for a solution in the (amazing complete and well-indexed) Vim online help (":help") and perhaps the Vim Tips site (http://vim.wikia.com/)
This goes for Emacs, too. I get the feeling I've never really used these tools the way they're meant to be used.