As far as the compromised key issue, all I can think of is getting another server to sign a timestamp + btct.co data at the cost of another extra step. Depending on how the mail system is setup now (I'm assuming one for trading activity that tells a mail server to send things), and assuming rooting one wouldn't mean definitely or possibly owning both servers you could have the trade machine sign transaction data and the mail server sign data+timestamp. Then as long as both servers aren't rooted you can't forge a timestamp that supersedes the correct data.
I'm thinking I'll create a key pair for all issuers when the security is created, then let them override it if they want. That way the users with existing keys should be good to go.
The mail setup would have to be altered significantly to do the staged signing, but it's a great idea. I'll have to think about it a bit.
Cheers.