The Bing toolbar only sends information back to Microsoft, it doesn't decide what to do with it. For this kind of a task it would be simpler to use a packet sniffer anyway.
On the other hand, if it uses the OS HTTPS infrastructure, someone could probably add a root cert to IE and "MitM" themselves. If it doesn't, it's just a matter of finding and replacing the key; while that's not completely straightforward, it is done.
Darn, now it's really tempting to fire up some VMs. I don't have time for that.