Ben,

Sounds like a great project. I would say you are starting off down the right path. My first suggestion is buy pro drupal development(if you don't already have it) by Matt Westgate and John Vandyke.

Currently, there is the ability to offer discounts based on role(Wholesale, Retail) using the uc_discounts module. You can find it in the Contributions section of the site.

I would say you are on the right track with your module list. Contemplate is very handy for custom theming. I always start with the Zen theme, then tweak it until it looks the way I want it to. Although I don't know of a way to have two separate teaser views, you should be able to use the taxonomy position manipulate the teaser view to what you desire. Example, the term has children, than the teaser output would look like Cigar_cutter_family_page.pdf. If the term does not have children, than have the teaser view look like Xi1_model_page.pdf. Check out the taxonomy module for more info. You could do this with contemplate, but you should consider using your own custom module with hook_nodeapi, and some Theme overrides.

As far as the 3rd party inventory integration, I would just write an export script to do that. Select all the orders that have not been exported, load the order, output the data, set the exported flag.

If you need more detailed information let me know.

Mike O.