Importing & Custom Capabilities

Here’s my situation:

I have a bunch of users, with different sets of custom capabilities, each one represents a product. From time to time I get new members for a new product, and I manually import them into the system, about 50-100 at a time.

This is because there’s no way of offering new customers (i.e. people that aren’t already members of my site) a way to buy a specific product on their own if the product is not set up as a Role (and I have more products than s2m roles).

Most of them are completely new, so a new user is being created with the new custom capability I have in the correct column in my CSV, which is great.

However, some of them are existing customers, with different existing sets of custom capabilities. These are not updated at all, and therefore do not get the new custom capability, which is the big problem here, since I have to manually seek them out (or wait for their complaint) and manually add it to their profile.

I was wondering if there’s a smarter way of doing this.

Any suggestions would be very appreciated!