Link directory in Rails - easy?

Hey All, hope someone can give me an idea of how easy/difficult it would
be to to create a link directory in Rails.

Here's a brief spec:

- People should be able to create an account and submit a link, either
to a category or just tag it with some keywords.
- There should be an option to allow people to 'buy' premium listings
(via paypal) which would then show above the 'free' listings (and they
should be sent an email reminder when the premium listing is due for
renewal)
- There should be an upload facility so they can submit a picture with
their listing. (And staff should be able to approve these before they
are made live)

Optional - as 'free' listings will require a reciprocal link, it would
be nice if the Rails app checked the persons website (once they entered
the url of the page) for our link... and maybe once a month too. Would
be nice but not essential.

Is this easy for rails? I'm a nube so would like a relatively easy
project to start off with! :slight_smile: