Integrate Membership with Database and User Uploads


I apologize ahead of time if this is too broad a question, but feeling a bit overwhelmed with the number of plugins and themes I now have access to.

Here's what I'd like to do:
1. I want people signing up for membership to answer a lot of questions that basically sync with my Aweber account or a database that could sync with Aweber, and only then have access.

2. People will be submitting both submission agreements and written pitches. I'd love to have them type in information that would then populate a PDF they download to sign.

3. I want to create forms that include file upload, for both the signed forms and the additional materials they'll be submitting. I'd like to say where those uploads should go, and ideally, I'd like them to go to a dropbox account with a specified folder. Ideally, this uploads are added to the aweber database or some other database.

I also own Gravity forms, which can do some of this, but I was wondering if given all the WPMU resources I now have access to if some of the are perfect solutions to what I'm trying to do, either plugins or themes.

Thanks for any assistance. I realize you probably can't answer all of this, but anything would help.