Update 18 June 2010: Upgrading WordPress.org has been easy because it is done within the admin site.
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Update 17/07/09: Upgrading to version 2.8 and 2.8.1 is a total breeze. 
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WordPress
I have a new blog at Writing Consultation (WC) and I decided to upgrade WordPress 2.7 to 2.7.1 but unfortunately things didn’t work out the way I expected earlier.
First of all, I thought that I can use the Automatic Update but it didn’t work at all.
So, I decided to manually upgrade.
To make things worse, I messed up with the whole database and WC ended up down for some time.
What happened was:
- I deleted all the files in the server (I thought I was supposed to delete all the files)
- Thank goodness, I have a back up of everything I need to restore my blog so once I restored my blog, I took some time to read through WordPress guidelines over and over again.
Basically, what I did after reading the guidelines was to give it a try again (even though I spent hours just working through the trial-and-error).
Step-by-Step guideline from a noob:
1. Because I am using WordPress 2.7 so I need to keep these files intact:
- wp-content
- .htaccess
- wp-config
2. I also use Sitemap (XML) so I have to keep the file as well.
3. Everything else not mentioned here is to be deleted.
4. Deactivate all the plug-ins.
5. Download WordPress 2.7.1 and unzipped the file.
6. Upload all the missing files to the server (to replace those files that have been deleted).
7. Go back to http://site.com/wp-admin to check if everything is ok.
8. Activate plug-ins after you have updated those with new updates (or keep the old ones even if without new updates).
9. View your site to check for any errors.
10. If no errors, you are done! If there is any errors, check with WordPress Support.
Lorelle from WordPress helped me through the upgrade. If you have any questions, you can ask Lorelle on her blog.
Good luck in upgrading!
Have a good weekend!