User Accounts Categories (or other method?)

Building out a Chamber of Commerce website and need advice on ways to approach some trouble items. Here’s the way I want the site to work, with additional would-be-nice items at the end.

I want a user to be able to register for an account for their business. This will be a form that includes uploading a business logo, storefront photo, and staff pic as well as adding contact info, and a short business intro.

Here’s the first catch: I want to let the new business select up to three categories that describe the business. For instance, a restaurant might select “Prepared Food”, “Food and Dining” and one other that makes sense. How do I get a list of categories tied to users that can later be filtered? When I go to the Business Listings page I want to be able to filter by type of business. So, I’d select “Food and Dining” and get a list of member restaurants.That’s the primary concern.

Nice to have would be the ability to pay and renew membership using PayPal that would automatically trigger a new renewal date on the account. However, this also needs to have a manual override for users who choose to pay by cash or check instead of online. (one workaround could be to have those users pay by cash/check and then I manually go and pay for that user in That would be a huge pain.

Seems to me these items have to exist in WP, but I haven’t found them. If there instead could be a way to create a type of content that is tied to a user account and is their business profile so I can use blog-like categories and tags, I’m game for that as well. Please point the way.