Design an account space section for paid directory members

My site has three user types. I'm only having issues with the one user type--the paid user. I'd like your help to design this paid member account area and profile building process. I have a basic user flow from sign up for how they create their profile, but I need to simplify how they create their profile, pay, and do other tasks required to set up the profile correctly. Think of it much like how you set up your Freelancer account, how you built your profile and added portfolio, and did email, text verification, straight through the payment options, and then to edit everything. There's having the paid user fill in the details of their profile, education, experience, portfolio, certifications. There's how to access the basic account/profile information. The biggest UI challenge I'm having is how to integrate the Choose your plan or membership option or how to get them to pay because what plan they choose depends on how they get to create their profile. YET, I don't want to have the user have to pay "upfront" without knowing exactly why one plan is better than the other, that's a fail waiting to happen. I need to integrate, you want to be in more "categories" or add more "skills" or add more "portfolio items", then that puts you at the Pro level. I have three levels right now, Basic, Plus, and Pro membership levels, but I'm having a hard time justifying the difference. I think if we can clarify the UI, it will help me determine the best route to take because I'm in a box right now. I have a lot of elements designed already that we can integrate. We did screenshots for this member section, but we realized in the process that they aren't adequate or clear enough. It's just not intuitive as is. Please have solid UI experience. I'd prefer if you had some membership website experience. Please send a brief note why you'd be a good fit for this project and some examples.