You say that Google will be doing this transition along with everyone else, but you won't be feeling the same pain. Google's current cert expires November 24th, 2014, so when you extend it then it will be for 1 year and your new cert will expire before January 1st, 2016 which is pretty convenient for you because that cert (even if it is SHA-1) will still show up as a green bar through Chrome 41 so it will have no impact for you. I also second eastdakota's response that this was pretty crappy to drop as a Friday afternoon announcement.
(Google's certificates only last three months and that's not because of this announcement.)
The transition that I'm talking about is the transition to SHA-256 overall. If you're in a position where your CA sold you a certificate that they shouldn't have then I feel sorry, but if you're blaming us for that then I think you're pointing in the wrong direction.
I would guess that most buyers of certs are not technically sophisticated enough to know that they should have been looking for a cert with a specific encryption algo, especially if they bought a very long-lived cert x years ago. That said, I'm guessing that most reasonable cert providers will allow reissues.
What would be the technical challenges facing offering free wildcard certs? Is it just engineering time, or is there something more fundamental? That seems like it would do much more for web security than pushing for higher minimum encryption standards on certs would...