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I've decided to finally "come clean" on this topic. I know "conventional wisdom" among sax players is to never touch a rolled tonehole with a file for fear that the rolled portion will be completely filed through. However, I have found a way that it can be done safely and have done it on several vintage instruments.
I strive to make the toneholes perfectly level when I overhaul a saxophone that has rolled toneholes. The first step is to mechanically make the tonehole as close to flat as possible by lifting low areas and tapping down high areas. Then the tonehole is carefully and judiciously filed using a rotary diamond file. Care is taken to never remove the amount of material it would take to go completely through the rolled portion. The next step is to use magnification and sand the "corners" that have been created using craft sticks starting with 240 grit and finishing with 800. The illustration below shows the basic process. The amount of the "circle" filed off in the picture is much more than would be taken off leveling the tonehole, and is shown "exaggerated" to make the steps more clear. If the tonehole is on a silver plated saxophone the sanded area is touched up with a silver plating wand. If the tonehole is on a lacquered saxophone it is left as is. At the end of the process it is difficult to tell the toneholes that have been filed from those that have not.
I strive to make the toneholes perfectly level when I overhaul a saxophone that has rolled toneholes. The first step is to mechanically make the tonehole as close to flat as possible by lifting low areas and tapping down high areas. Then the tonehole is carefully and judiciously filed using a rotary diamond file. Care is taken to never remove the amount of material it would take to go completely through the rolled portion. The next step is to use magnification and sand the "corners" that have been created using craft sticks starting with 240 grit and finishing with 800. The illustration below shows the basic process. The amount of the "circle" filed off in the picture is much more than would be taken off leveling the tonehole, and is shown "exaggerated" to make the steps more clear. If the tonehole is on a silver plated saxophone the sanded area is touched up with a silver plating wand. If the tonehole is on a lacquered saxophone it is left as is. At the end of the process it is difficult to tell the toneholes that have been filed from those that have not.