GeorgeF-
1) This depends on how the allow rule is configured. If it uses the certificate that signed the app, then doesn't specify a version, then a new version of the same app (presuming it is signed by the same certificate), a new rule would not be required.
2) The only way I know would be testing. If you allow an installer to elevate because the installer requires elevation to install, the actual app executable can be a different file. If they are signed by the same signing cert, you can create a certificate based rule that allows anything signed by that certificate. But you should be careful with this, as it can allow anything singned by the cert to elevate, and you may not know what other applications are signed by the same cert, and they may be dangerous to allow to elevate.