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Ok folks, I hope I do an ok job of explaining what I am asking....

I want to use a dual band 2m/440 rig in crossband repeat mode and also use a 2m amp on the 2m side. Is this possible on a newer rig with built in duplexer and only one antenna jack? Can I pass a 440 signal through the 2m amp without messing it up?

I am GUESSING that you would do more damage to the radio than the amp. It will sense the RF and key but will create a mismatch in the tuning circuit. If the amp is relay keyed instead of RF sensing, you could get by with bypassing it with a hard switch. It is likely to be a problem.