How was he allowed in with a canceled visa? The visa sticker would have a marking or written/stamped "used" on top. Do you in stead mean he had an extension from a non b with a reentry permit? A stamp from an immigration office that is. In that case maybe it wasn't actually cancelled, and he would be on overstay now. Even though they stamped him in again, the base for that stamp was no longer valid, if he did not work anymore.
No they wont because your visa is already expired at 19th october this year and you won't get anymore stamps out of it. You can keep your current stamp alive with reentry permits, but you will not get any longer stay than you already have on it now.
maybe that's the case. They did say they would have accepted it for extending based on over 50 though. But the amount was to small per transfer. But being Danish (from Denmark) he could not get that notary letter. As mentioned they do make an alternative one now. And that was accepted.