Multiple Update User Roles in One Form

I have a two-step user registration form on my website. First, the user agrees to participate on my website and through a Gravity Form, they create a 'basic' user account. Later on, they go to a page where they choose one of four paths in which to navigate the website. I am attempting to use the Update User option so that once the user chooses a particular path, their WP user role will turn from 'basic' to 'path1,' 'path2,' etc. However, it appears that I can only update from one to one, not one to one of four.

Right now, to get around this, I have the user choose the path they would like to take and then press submit. That takes them to another page where they confirm. I can then use that conditional confirmation to add them to the path they have chosen.

What would be great is if I could lead them from 'basic' to one of the four paths all within that one Gravity Form. Is this possible?

Thanks,

I am too. I have a winery client that wants users to be able to join 3 different levels of wine club. I'd like to make that a dropdown on the form with a description of the requirements next to it. All that is doable without writing code except for mapping the values to different roles.