The replacement tierod ends do not need any taper in the arms, they are a straight shank with lock nut. Its a direct replacement for the ball and socket. You can drill out the ball as long as the drill is not bigger then the new tie rod. You won't need to drill all the way, but if you do, its not the end of the world.
$30 is a good deal on the sector shaft, and like Yar said, find you a local bearing supply and pick up the new bushings, they a really cheap to purchase. You will have to cut your self a new gasket, but thats pretty easy to make. The worm shaft bearings are a odd ball and probably won't be avalible local if you need them. The Filling Station has them seperate.
The top bearing should be fine, its the lower one that gets water and dirt in it. The seal is the same one GM used clear up through the sixtys or later, any manual steering box uses the same seal.
Joe