This is a very thought provoking question... my experience with used saws is 50:50. The used saws that I should not have bought were procured when I didn't know any better. The used saws that I bought that have worked out were great deals that saved me hundreds of dollars had I purchased new.
My experience with new saws is the same. I bought an 029 because that is where the dealer steered me, not thinking that was where his best margin was. The saw worked fine, but it didn't take long to realize that it wasn't what I needed. My eBay special 3450 impresses me more everytime I use it, and I paid $100 less than what the box store is charging.
I think I gotta go with Rocky though. If I were making a living with my saws, I'd go new. As you get experienced, you get a feel for the good deals, whether new or used, but with new you have the warrantee to fall back on if things don't work out.