You're not an idiot and there is no such thing as a stupid question.
There is a product that I've had very good luck with called Seal-All. It is gasoline compatible and does a heck of a job sealing the intake at the carburetor. It looks and smells like old Ambroid model airplane glue but does the job. I like to fill the slots in the carb throat where it clamps to the intake manifold to assure against air leaks. Also check carefully the gasket sealing at the intake manifold and the cylinder. Give this a try and get back to us with the results. The only thing that concerns me is your comment "at least now it will run with a choke" What do you mean by that? The choke should be wide open (lever fully down) for it to run properly. Good luck.
Age and Treachery Will Always Triumph
Over Youth and Skill & "Charlie Don't Ride"