How Bad Am I Screwed? :(

if you drill and tap try to put the trans so the the hole is pointing to the ground (so as you drill the drillings are falling toward) also use some kind of grease then if you can with the hole still facing down somehow try and flush for ATF to help clean it out welding the hole may not work remember Aluminum is very porous and soaks up oil
Did you ever here of JBWeld I use it for everything with lots of luck. They also make good epoxys.