Customizing very heavy

Hi, I’m trying to do a little online portal to sell used items. I created two types of categories: the categories represented by the name of the city and the categories that represent the type of object to be sold. I would ask if there is a very customizable plugin, allowing the visitor to enter the post for the sale of his object at the same time while registering to the portal, so that the visitor has to click on a link on the first page ex “insert post”, chooses the name of his city by the list of cities, click the name of the object category, enter a title, a description, insert one or more photos of his object, his e-mail address, he has also to check the “I accept the agreement” check, and, clicking “ok” button, he automatically receive an email with his username and password to edit or delete his article.

I must ensure that visitors of the site when they find his post and consider it interesting, they can click a small button “contact user”, and send an email to his email address using a form mail.

Is possible to make something so complex, using plugins?

Thank you very much.