Team Site with Membership and Store

I’m trying to find a better way of managing our team. I’m thinking that WordPress could solve all of our problems by compiling a few different addons. I’m looking for recommendations and to have a discussion about the functionality we are looking for. Much of what we do today is very manual, and this should hopefully help reduce the overhead of some of these items.

I’m not certain that all of the functionality we are looking for even exists. Do you have a site that is doing anything similar? Do you see anything I’m missing?

I think that WordPress solves most of our content needs out of the box.

Membership Registration: We have paid and unpaid membership. Paid membership comes with the ability to purchase clothing and entitles the member to one free jersey per year. This must also have a backend for updating payments when someone pays via check.

Store: One free jersey per year. Other clothing for sale. Order statuses provided to user when clothing has been ordered (in batch) from the clothing vendor. Would also be nice to have a status for orders to let them know once they are being shipped.

Calendar with EventBrite Integration and File Attachments: We attach route maps to our events and we like to use EventBrite for collecting RSVPs to the events. The events can be attended by people who are not members.

CSV Report Extract: Role based extracts for Treasurer, Clothing Order, Communications Chair, etc.

Newsletters based on membership roles: We would like to send different levels of newsletters on a regular basis to people involved with the team. Some people are riders in particular events and we would want to send them specific sections of the newsletter, but those parts may be irrelevant to our volunteers.