I’m going through the process of upgrading any number of the 139 themes and 76 plugins we have available on the J-School network. One thing I do on a regular basis is write a short blog post listing the affected software and what’s new. Unfortunately, I think few people actually read through these.
What would be more awesome is a personalized email to site admins listing the software updated and notices from related change logs (all automated, obviously). This is completely doable.