ACP->vB Settings->User Profile Options->Allow [IMG] Code in Signatures
Set that one to Yes.
Now the scenario with controling the use of signatures with the usergroup permissions should work.
Edit: Oops didn't reread you first post correct.
If you want all user to be able to use signatures, but only a few to use IMG tags, yes then this would require a hack, moving the IMG in signature permission to the usergroup instead of only being global.
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