A lot of this hassle can be reduced by installing drupal from cvs rather than installing one of the releases, and by keeping your installation under version control
All you need is Capistrano and an account on the deploy machine. This can be used and extended to deploy to several servers (also at once), move databases around, etc. The gain is that you don't need to login to the server. We can talk about that interesting technique tomorrow.
Unfortunately, while Capistrano is all easy to use with Rails, I had to write a custom Drupal-tailored Capfile.
Using CVS to maintain a Drupal website
