Can you record and listen at the same time on the same channel?
On the Stiletto 2, yes you can. But, be careful: do not erase the recording (in the Library) before it has finished recording, otherwise, you'll almost surely corrupt the file system and get intermittent problems in the future.
My experience is that, when a show has started recording before you actually tune in the channel, you should "rewind" a few seconds, otherwise the Stiletto will eventually (between 2-20 minutes) stop playing music and return to the main menu (while still recording). If you rewind, it will behave itself.