Upgrade/update process too cumbersome

I've harped on this before so I apologize for returning to the same subject. But I just checked a website after a couple of months and find there are a bunch of module updates needed, many of them security issues, and a new core security update. I'm starting dread running the status report because it's such a cumbersome process. I've heard that updating a site takes 15 minutes, but it takes me 2 hours, and it seems I always end up with plenty of errors and confusion! CCK fields go missing, or I forget to turn off a contrib module, etc…. I just can't imagine that everyone who uses drupal is not having the same issues? And as I now have three drupal sites running and many more planned I'm getting worried that the process will become overwhelming.

With everything else that is so awesome about drupal I can't understand why all this update process is not automated? I’m will forever be a newbie with limited programming skills. I hope version 7 will fix streamline or eliminate the update process.

I’ve assembled a list of modules that help with the process below. But if you have any new ideas please let me know. I never got into the 'drush' thing because I completely didn't understand it, but it looks like I will have to take a better look. Let me know your thoughts on it.

•http://drupal.org/project/drush
•http://drupal.org/project/admin_menu
•http://drupal.org/project/devel
•http://drupal.org/project/backup_migrate which backs up the database.
•http://drupal.org/project/contrib_toggle which disables the contributed modules with one-click. (doesn't yet have 'enable' though!)

Please add yours.

I’ve also been told that I don’t have to disable the contrib modules, but every time I’ve run an update but I ran into nightmares when I didn’t. Below is the current overwhelming procedure I follow, and it doesn’t take into account that I’m meant to do this entire process locally before I do it on the production site! There is no way; (and I gave up on that because every time I try to publish the site locally, and/or back to production, I always lose all the images even though they are in their correct folder locations and I’ve never worked out why.) So I now just back up the database and files and run the updates/upgrades straight on the production site.

Here is the cumbersome procedure:
1. Back up database
2. Back up the files.
3. Put site in maintenance mode
4. Change from a contrib theme to garland
5. Upload new Drupal core (6.14 now)
6. Replace the Sites folder with my old one
7. Disable Contributed modules (thank goodness for the disable contrib toggle module)
8. Run update.php

As I have modules needing updating, I next
9. Remove the out-of-date modules
10. Upload updated modules
11. Enabled all the contributed modules (what a waste of time re-selecting all the boxes!)
12. Run Update.php again (no problems)
13. enabled theme
14. Put site back online.

So please give me your recommendations. This is all just too much and something always seems to go wrong! Let me know if Drush will solve all my issues and if you think I should take the time to figure that out? Or if you have any other modules or methods that will work correctly and safely?