Free Memberships for all but a variety of listing options? How can I achieve it?

Hi everyone. Here is what I am trying to achieve.

All memberships to my site are free, so I have set up a Free Membership but have it hidden as members don’t need to select it. Members can come along and list in order to recommend a place to the community.

I want to then be able to contact the business that the member has recommended and invite them to claim their listing and upgrade to a paid listing.

When the business is upgrading their membership I wanted the to be able to choose from a range of options. Option A might be 2 images and 2 categories for $10, Option B might be 5 images, 2 categories and a Featured Listing for $20 etc etc.

I am aware that Membership packages can only be linked to 1 listing package. So, my question is, how can I make this happen???

My site is http://www.worldschoolingcentral.com/wsc (preview URL as currently not live)

Thanks in advance.

Karen