Hi Chris,
Thanks for checking out our plugins!
You can indeed add 5-10 events to the same day, and there are several different options for displaying them. With the free version (The Events Calendar), you get month view, day view, and list view, and Events Calendar Pro adds map view, week view, and photo view as well. You can see an example of these on our demo site, wpshindig.com.
For event registration, we have Event Tickets, which will let you create free, RSVP-type registrations on events (and other post types as well), and Event Tickets Plus, which will let you sell tickets on your site and collect additional information from attendees when they register.
You can include a link to another page/flyer in the event description, and Events Calendar Pro also comes with the ability to add custom fields to an event, which you can use to add a link.
We do offer full refunds within 30 days of purchase, so if you’d like to take any of our premium plugins for a test run, feel free to do so! Please let me know if you have any additional questions.
Thanks,
Jennifer