But coaches flat out tell you "give me more money."
I agree this should be changed - it's undoubtedly not intentional, but just a combination of the fact that offering a new contract withdraws the existing offer and the system checks to see if you ever withdrew the offer before awarding a compensatory pick. And there's a good reason for the second part, it's just that they should figure out how to not have a new offer count as a "real" withdrawal.
But Mike's point is good advice - if you're not sure, ask.