Re: Subdomains and other questions
Hi. I'm also waiting for 2.9 so as to avoid the upgrade process.
I think I can help you with the first 2 questions as I think they are dependent on both your host and WordPress itself...
ClassiPress is nothing more than a theme for WordPress (although a unique one at that). If you want to use multiple sub domains, you would need to create them first, then install WordPress to each one. These would be completely independent of each other and wouldn't be cross-search able. Some basic info here:
http://codex.wordpress.org/Installing_Multiple_Blogs
You may get some help from your hosting provider on this... Don't be afraid to ask them, I'm sure they have many customers with multiple blogs.
Hope this helps.
- Dubya