How to list upcoming events with pictures and updating registration links?
You could try CiviCRM Event Organiser, which syncs events between Event Organiser and CiviCRM. If you create your events in WordPress via Event Organiser then each event can be assigned a Feature Image. Here's an example listing where some events have Feature Images. As a bonus for busy sites, you get a nice calendar that comes as standard with Event Organiser.

Sync works with repeating events if they are created in Event Organiser and then synced to CiviCRM - but not the other way round yet. Each event that has been synced to CiviCRM will have a link to the relevant CiviCRM registration page on its standalone page but it's possible to inject this into the archive template too.

It has to be said, however, that this is a fairly heavyweight solution and can take a fair bit of setting up so YMMV, caveat emptor, etc etc. I would strongly recommend installing on a development version of your site (or a test site) first.