Yeah claiming it almost a full month after is a bit silly. That would mean I can go back and claim free weeks and doubles weeks from previous years just because they weren't closed. It's like claiming welfare a full month after just because you weren't here to do so.
I would stoked if he didn't, than again I can't really say I'd be thrilled with him ended up in certain places (SF, Chi etc..) so Cleveland wouldn't be bad.
I don't know really, it's really hard to judge this one. I don't know if he can use the whole "I was woozy as a defense" considering he looked up at the linesman for 5 seconds got on the bench and din't go to the black room.
You create him in the Create-A-Player section. If you create him your previous player will auto-retire right away anyways (not that he was with a team at all).
Your best bet is to recreate with the same information. The only difference between recreating and keeping your current player is that you'd be one year older and your career length would be cut off by one year in reality.