I have a really interesting situation... inexperience is a heck of a teacher.
Looking at the picture it'll be evident that I had an idea I thought was good but the result proved the execution of the idea was not that great as I ended up with the tuning machines at significantly different levels which I knew would happen I just over did the sanding n the stock thus resulting in the 2nd string machine post being significantly higher removing any angle I had on the string. So high in fact that I am short on ideas on how to force the angle. One thought was using a drawer pull or an eye-bolt to pull the string down. I like the drawer pull idea but wonder if the upward pressure of the string wouldn't bend it and the idea of an eye-bolt seems to gaudy. Anyone ever dealt with this?
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Cut another piece of headstock, glue it to the bottom of the existing one, and remount the tuners?
Though about doing just that - the headstock has a significant contour underneath hand shaped so I'd have to cut off a good part of the existing one to get a good flush surface. I did cut a small piece to act as a spacer I can put under the machine head which was my last resort if I couldn't score a decorative yet functional option.
Brendan's idea sound quite aesthetic, add another layer of fingerboard and shim up the nut, so you can keep the unique interesting headstock.
I like all ideas, I don't have a fret board so I could pop a 1/4" on top. I did add a shim to the nut but still didn't get enough break so I don't know if the extra work will yield the result. I thought using a drawer pull as a string tree behind the nut would be a nice option since it can look intentional and not overdo the break.
It looks like you have a taper on the upper and lower surfaces of the headstock, in which case a string tree may be the easiest solution. The string furthest from the camera seems OK, so maybe a washer and a screw would do the trick for the other 2 - like on a Fender bass.
ETA: The Fender bass string tree is a bit more than a washer ......... but not much ;-)
Both are indeed tapered and the bottom is beveled sides and a bit curved from back to front. It's the back machine only that is the problem the other 2 break nicely. The big concern with the typical string tree is the string is so high that I am afraid with use the screw will pull out from the tension and tuning.
I had this issue when I first started....and my way at that stage of my building experience wasn't enough too know what other options I had too fix the issue. So what made sense to me at that time was too leave the strings a bit longer.....and when wounding the strings I made sure that the main part of the string wound too the bottom of the post, rather where if it were too end up on top you'd have virtually no string angle and well we all know what happens after that...It worked well....but as I started seeing alternate methods, I changed my method for the better.
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