I encountered some strange behavior with the "Jump from an airplane!" contract. I put a kerbal in a command seat and a parachute on a decoupler and released it above 2500m. The contract didn't recognize that (not sure if it's supposed to; in the OP you recommend SM CHUTE, so maybe not). The weird part is that after I landed the plane, when I exited Jeb from the cockpit, the contract completed. It seems like it didn't check whether his EVA happened above 2500m.