The most recent thing i saw was Strong Bad doing let's plays on ancient games, including modding them on the fly, which was highly entertaining:

https://www.youtube.com/watch?v=yvscxQN1JlA&list=PLSFI7mabpY...

Matt Chapman has a day job as animator/writer at Disney (https://www.imdb.com/name/nm1480095/). I'm not sure what Mike Chapman is up to. They still manage to put out H*R content every so often. Usually it's just a yearly Halloween costume montage, but there have been a few small games like Marzipan Beef Reverser and the recent Dangeresque point and click adventure remaster that released a few weeks ago.

Not a Homestar Runner show, but they were heavily involved with Yo Gabba Gabba.

Not that I'm aware of, but they did have a videogame