Have a question about upgrading customers of individual applications to a bundle of software that includes their currently owned application.

I used to sell a bunch (5 different stand alone products) of financial reporting software products to the enterprise. Early this year I collapsed all of the products into one "bundle" (they work closely together, so it doesn't look like it used to be 5 apps – is more seamless ) – so now I only sell one SKU.

The individual products all were sold per server at different price points. The new bundle is sold based on "Named User".

There are older customers (anywhere from 6 months to 3 years) who want to move from what they currently have to the full bundle. Some own just 1 of the old standalone products, some 2, some 3. None owns all. All are current on their support agreements (customers number in the hundreds).

My question is: what are the best practices around how I sell customers the bundle when they are upgrading from 1 (or more) products that are now included in the bundle?

Do I simply discount and terminate old licenses?

For every old product and combination of old products do I need to define a precise path and/or migration SKU (would be a lot of work)?

Do I give different levels of discount based on the amount of time they have owned the product? Or how many products they own? How would I assign these? I could try to figure out the weighting of the value of the product(s) they currently own (vs the bundle), but will be a bit challenging due to the change from server to named users and since some products run on one server, some would be purchased for more.

I would like to keep this as easy as possible to manage, and give my sales team flexibility in how much they charge for the upgrades.

Any advice would be a big help - thanks

Tim