You are over-thinking this: remember we do that when there exists no easy way to gain preapproval; so the owner's attitude is going to be whatever it was before we asked for permission.
And: let me see, once licensed, we all have the right to transmit on GMRS frequencies with or without tones. Doing so politely to ask for permission to use a repeater, maybe be, in your opinion, breaking into his system. But to me your conclusion is a bit over the top!
Then go back to your original suggestion: Roll the dice and donate!