Here's an idea... Multi Column PLUS
Don't know if anyone has thought of this yet but here's a mock up of what I had envisioned for my Classipress website, but I don't know how to implement it. Eric Hamby (taylerj) might though!
Two major features...
3 Featured Post Columns
Top 5 Posts From Each Category Displayed in 3 Columns on Home Page in grid view.
Thumbnails still visible with bolded price on each ad. The only page that would change is the home page, and columns are easy enough to do as implemented on http://www.swgdirectory.com/
The only issue I think would be to call the top 5 ads from each category and display them on the home page in the way I have designed in my mock-up.
What do you think?