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NO, do not 'dress' the end of the shaft to fit the coupling! The coupling is made out of cast iron and will corrode. The shaft is stainless or perhaps bronze - stable materials. The reason the fit is tight is that the bore of the coupling has corroded.
I recommend you get a dowel about 1/8" smaller than your shaft, wrap some 80 grit around it, then clean up the inside of the coupling. It won't take much work as you're removing rust, not good metal.
Again, you need the drill recess in the shaft to take the cup point of the set screw. Measure the cup point and you'll know what size drill to use. I recommend a cobalt drill for cutting stainless - HSS will just burn. I also recommend a drill press!
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