On the boom, seems you could just put an eye strap on the bottom of the boom if you just want to shackle a block to it? That's what my B-32 has. With a bail, if you use lock nuts, you really shouldn't have to tighten them down that tight since you do want the bail to pivot some. Put nylon washers between the bail and boom. While you're at it, think about putting a bail at the aft end of the boom. Comes in handy for hauling someone out of the water, lifting a dingy or hanging in the water from a bosun's chair. A compression sleeve is a good idea, but at the cost of a larger hole in the mast. It may be some work, but maybe you can manage a sleeve installed from one end of the end of the mast. That way, you'd only need a hole the size of the bolt.
On the pole eye, someone "in the industry" said to mount it on the front of the mast, at the gooseneck height. That way, they counteract each other. Personnaly, I like the suggestion to mount it at the clew height of your most-likely used sail. Remember, that as the sail fills and lifts, the clew will rise also. At the dock you might attach the spin pole to the clew, extend it if adjustable, make it horizontal then mark the mast at that point.... I placed a second eye 10 feet up the mast to hold the upper end of the pole. With one of those rubber mast pole brackets in between the eyes, you attach the upper end to the eye, "pop" the pole into the rubber piece, then attach the lower end of the pole to the lower pole eye. No rattle!
If you through-bolt, don't forget the compression sleeve. 
