I too do it freehand. As you dad did, I clamp the bar in the bench vice. (actually I have an old bar I can lay the chain on,) and I use a Dremmel tool with a grinder that is the same size as a file would be for that chain. Look at the way the chain is currently ground, and with file (or Dremmel) try to lay the file against the chain to provide the same angle(s). Once you're confident on the angle, go ahead and sharpen. You need to file until there is a sharp edge appearing on the top of the tooth. After a couple sharpenings, you may need to take the tooth off a little on the tooth that leads the cutting edge, as that controls the depth of the cut. I never had good luck with a file guide, and had one of the best (most complex) and files went dull on me in a couple sharpenings. Carefully used the Dremmel lasts quite a while, and produces results - fast!
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Today's Featured Article - A Cautionary Tale - by Ian Minshull. In the early 1950s my father bought an Allis Chalmers B and I used it for all the row crop work with the mangolds and potatoes, rolling and the haymaking on our farm. The farm and the Allis were sold and I have spent a lifetime working on farms throughout the country. I promised myself that one day I would own an Allis. That time event
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