I haven't used Drupal in quite some time, and have a large amount of experience with WordPress. I suppose I've become somewhat spoiled by their easy updaters.
The first issue I'm having is just using the admin to update modules. When an update comes out, I select it, then I get sent to a page to enter my FTP information. Well, the server this is on (I'm using Quickstart 0.9.1 for my working copy) doesn't use FTP. Everywhere else I've read it will do FTP and SSH, but FTP is the only option for me in the pulldown and my SSH credentials don't work.
So I tried to use drush yesterday and it didn't work either. I looked at http://drush.ws/ but the info there seems to assume you already understand how it works. I tried pm-download and then pm-enable but neither resulted in anything. pm-download didn't put any files on the filesystem.
Manually updating is obviously an option, but the problem I have with that is I'm using SVN and erasing the old module directory also removes all the .svn files associated with it. So then I have to make a copy first, then manually copy those over. That's not really a good solution. (I'm using Versions on OS X for SVN. The repository is on a remote server, and my working copy is shared via AFP and it's the drupal site on Quickstart.)