Letting Customers switch easily from Non-Memberships to a Paid Membership on the Customer Side

We allow Non-Members to upgrade their membership on the customer side if they want to change to a club membership. Due to CR's restrictions and quirks, once they add a Family type membership, the individual type Non-Member membership does not get removed, so CR sees the account as a Non-Member type still. This causes lots of issues for us and the desk has to constantly manually make changes, like going into the account and dropping the Non-Member status for each family member. CR support's suggestions to get around this require even more manual work, for both the customer and the staff. There needs to be an easy solution. If someone changes to a paid membership from a Non-Membership, the system should realize the the paid membership takes precedent and it should automatically drop the old membership.