After hours of searching through all of the WordPress calendar plugins, I finally found the plugin that does what I was doing over at WordPress.com: ICS Calendar feed.
If you like the “Upcoming Events” feed on this site and you run WordPress, that is definitely the one you should be using.
Why so picky? Well, for the live broadcasts, I need to let you guys know when they’re coming, and logging into the website and doing it that way is a hassle. I prefer to just update my email program’s calendar (in this case Windows Live Mail) and let the plugin do all the rest. Of course it handles Apple iCal, etc. And even better, it displays upcoming events as a list rather than some gigantic calendar with empty days and tiny text or worse, a separate page.
I kept skipping over it when I was digging around because the plugin site gave the warning that it hasn’t been updated in over two years, but it works fine, and frankly, good things don’t need to be changed!