Dougster, First off, when you get that new bit for your air hammer, grind the leading edge to a nice smooth radius so it won't snag on the bushing and chew the shnickers out of it. Bushings are expensive to buy, expensive to take out and expensive to put in. Then cut a piece of brass or wood and put it between the bit and pin. You can quickly mushroom the pin and that makes it "hard" to remove. If you have a garage with a stout header, you can chain the boom / dipper to it and with a chain fall or come along, remove all pressure from the pin. A large engine hoist may do the same thing. If you don't remove the pressure, it won't come out easily. Also, if you don't have any way to move that awkward and heavy chunk of metal smoothly by thousandths of an inch, I don't think you will get the pins back in. Having it balanced in the air by a chain so you can wiggle and jiggle it is the difference between getting it back together and learning a whole new set of cuss words.
Next, if the pin hasn't been out in a long while and possibly hasn't been lubricated, it may be grooved. The non-wearing areas of the pin may be quite a bit larger than the worn spots. That can make them catch on the bushing and be a real bear to take out. Also, if they are that worn, the bushings probably are too. If they miraculously were not worn, driving the jagged edge of the pin across them will typically bugger them up bad requiring them to be replaced.
Have you gotten a list of all pins and bushings for each joint that you are going to mess with? You should, so you will know just how much the replacement $$$ will be. Pins and bushings can easily run over $1000. If you need a machine shop to replace bushings plan on about $50 - $100 per bushing. Smaller is cheaper, your hoe is probably full of smaller cheaper bushings. Also, if you do go to a shop make sure, in writing on the work order, you add that they are not allowed to use a cutting torch to remove the bushings. It's commonly done and it nearly always grooves the housing and messes it up bad.