I don't even think that is a stupid thing. Hal became a pilot because he loved the thrill of flying, of staying in the air, only relying on his own skill as a pilot. The ring sort of constrains him that way. Its a like an infallible safety net. It takes all of the thrill, all of the skill out of flying. The way Hal sees it, he might as well just crash his plane, cuz he knows he's gonna be okay. It takes away the "art" of flying for him. Its not stupid to want to put your skills to the test.