Well, I know what I would do now, if and only if the chewtoy thing still bothers you. It would bother me, it's kind of hard not to see. In the 2nd picture of your 2nd post, it looks like you have pretty much the full thickness of wood behind the front outline. This is a good thing - there are certain really rounded, melty kinds of Telecaster headstock carves, the vintage guys go into spasms over it.
What I would do with it is make it into a 4X2 headstock, with the two highest string tuners over on the other side. Saw off the top and give it back to the dog. You'd have to bag those Kluson tuners and get something small and self-contained, the Gotoh SG-38's that Warmoth sells are great for the money, or the small Grovers, or even some Ping's can be fine tuners, branded or not. The tuners on there are known as “left”, they just are. If you use 6 left tuners, with the two treble side ones you'd actually want the strings to go up over the outside of the posts, and the tuner itself would be closest to the center. It wouldn't be hard to track down a site that sells both lefts and rights, and get 4 and 2. Then the strings would ride up the inside of the head.
It's going to look weird, no matter what you do – so it has to be done really, really nicely. Make up some crap about the vibratory de-tensioning relay waveform or something, better than the shaggy dog story anyway. It will have basically no effect on the playing, tiny differences in string tension and weight distribution is all. I'm not going to go wide and deep on this unless it sounds like something you'd really like to do. In that case, the first thing to do is go to one or another of these two sites:
http://shortscale.org/forum/viewtopic.php?t=38813
http://www.gitarrebassbau.de/viewtopic.php?f=10&t=6&start=0
Dig up a Telecaster headstock and print out half a dozen. Get your tracing paper, pencils, erasers, crank up some loud but intelligent music...