So I went to yutorah.org and downloaded some shiurim (Torah classes). My search criteria (language=Hebrew, topic=something related to whatever Jewish Event was coming up) were nice and vague while still narrowing my results to a manageable selection. I quickly settled on a particular rabbi, who happily not only gave classes that fit my search criteria, but whose actual content happened to dovetail beautifully with my interests. I'd never heard of the guy before (and still knew almost nothing about him, other than that he's clearly a native Hebrew speaker), but I love his classes, and that's what counts. (Seriously. It's gotten to the point where I've caught myself hoping for at least some traffic... Enough to listen to an entire class, let's say.)
Then B2 sent me a video of Purim at his Rebbe's house, and I see a guy dancing who looks just like the stock photo next to the classes given by the rabbi I like so much. Yup. Turns out that the made-for-me classes that I stumbled across are given by none other than my brother's Rebbe.