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Pricebooks & discount management for customers

Our company has 20,000 products that we currently manage quotes for in a 3rd party system which we sync with as opportunities via the Force.com web API.  


We are a distributor and sell to resellers.  Most of our products have variable cost & sell price based on the type of reseller we are selling to.  For example "Gold resellers get 20% off list price on the product category abc" - and that's how we determine the quote price on a line item.  Because we are a distributor some of these pricing rules are not our choice, they are provided by our vendors we distribute for.  Currently we determine price based on a discount management system where we pass the customer ID, the vendor ID and the category of product and it responds back with the % discount for both our cost & the reseller price.  


I'd love to start using the quote / products & pricebook objects in salesforce but i'm struggling trying to think how i can do this in salesforce.  


Any ideas would be appreciated!