Will Wordpress.com business do everything I want?

I want to create a site to display content for students to support their learning.

This will include a number of faculty areas that then drill down into subject areas. Each subject area runs a number of courses which in turn have a number of units. Each unit will contain content that includes text, images, external links to PDF's and embeded video and other embedded html for things like games and flashcards e.g. quizlet.

I have mocked something up in wordpress.org but I am wondering if wordpress.com would be able to satisfy everything from the above?

If in the future I decide I want to move from .com to .org can I download and transfer it?

Do all the plugins come with wordpress.com that come with .org on the business plan?

I would also like a section of the site that would host a job board for work experience, is this possible in wordpress.com?

Many thanks