Registration & Submission of Application

Hello good people. Here’s what I would like my job board site to do, and am wondering whether someone has ideas (plugins, codes, etc) of how I can make it happen.

1. When users register I would like them to upload more than one document. At present there is only the option of uploading a CV in .pdf. Is there a way they can upload more, e.g. cover letter, transcripts, references, etc?
2. I would like users to apply for a job by selecting which of their uploaded documents to attach to their application. Following step 1 (above), a user may upload 10 documents but not all of them may be required for all vacancies. I’d like them to select some, not all, documents to send.
3. When users send their application I would like it to go to the employer directly. I could also receive a copy of the application as the admin…but I want the application sent to an employer’s e-mail address which I will attach to the listing.

Is there a way these can be done?

Thank you!