Well I sure picked a bad couple weeks to volunteer to send a bunch of Bitcoin test transactions...
While I tested less than I would have liked, there are some notable results:
I think these results really show there is no reason to try to maintain the old-software-can-send-to-future-segwit-versions property, given that more than one not just didn't support it, but actually sent coins into a black hole.
Thus, I agree with Rusty that we should change the checksum for v1+ unconditionally. That also means that old senders are protected from the insertion issue (by failing, as we can guarantee that new-checksum addresses, even after a few errors, are invalid to old software).
Absent objections, I'll write up a BIP soon.
Cheers,
--
Pieter