The commentary isn't some talking head explaining the episode. The characters shrink down and act out the jokes themselves, tripping over their own awkwardness in real time. You watch Kyousuke fumble through explaining something obvious while Kirino cuts him off, and it lands harder than any standard voiceover ever could. This is what happens when a show trusts that its characters are funny enough to carry commentary on their own show. The compulsive rewatch factor comes from catching reactions you missed the first time, from expressions that deserve their own commentary track.
Oreimo Animated Commentary is a set of 16 comedy specials from 2010, tied to Ore no Imouto ga Konna ni Kawaii Wake ga Nai. The episodes were released as extras on the franchise's Blu-ray and DVD volumes rather than as part of the regular broadcast run.