Sure you can if the payee supports sending the transaction to the balance management database. The database will respond with a confirmation (digitally signed) which will then revoke the cool off time. The cool off time is there only to make sure that the database is up to date even if the payee doesn't support sending the signed transaction to the database for confirmation...
What if my newsvendor is out in his shitty little kiosk in the street? Cause newsvendors usually are.
Think of this as an equivalent for a debit/credit card; you'll need internet access for instant confirmation. :/ But the HW wallet could be connected to the internet, for example, through your phone using Bluetooth.
It could also just be GSM (I think is the acronym for what phones use?) enabled. This would allow usage pretty much anywhere.
That's a valid possibility.. Usage offline is possible too (like with the TREZOR), of course, but then it's just like any other bitcoin transaction; the payee's not safe until the transaction is in the block chain.
Yeah, I'd be wary of any offline-only system just because you have no idea whether or not it's actually valid. Could be someone that is going from person to person claiming they have x amount, then "transferring" and you wouldn't know until later.