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.

String tree will take care of the downward angle .....Last build for 2012

I hate string trees. Does your guitar have a fret board? You could add one, raising the whole shebang including the nut. My first guitar had a similar problem, added wood to the back of the headstock as RtoS suggested.

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.

Single string tree for the offending string, is the quickest, easiest solution, and takes less than 3 minutes to implement. Really tiny eyelet screws work fine. I have put some rather extreme downward and sideways angles on strings as mods on two different builds by two different builders using eyelet screws. As long as the interior of the eyelet is smooth ( and they usually are), you shouldn't have any problem. Use the smallest eyelet you can find, and crank it all the way down into the wood. Alternatively, a heavy electrical staple can do the same job, as can a simple panhead screw.

This one...

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.

Reeds ( and everyone else):

I wrote a song about this very thing several months ago:

As The Worm Turns (with apologies to Dr. Suess, Robert Service, Rudyard Kipling, and soap opera TV)

The twangers and bangers did all gather round
To cuss and discuss the details of their sound.
But one thing that stumped both the bright and infirm
Was the why and the which of the turn of the worm.

While some scratched their headstocks, and others their nuts,
The rest filed advice couched in ifs, ands, or buts.
"No skin off my nose," said the one with thick derm,
"I don't give a damn 'bout the turn of the worm!"

"I've never had failures, I've never had breaks;
This ain't like the Parsi Man's dreadful mistakes.
I just pops 'em in 'til they stand proud and firm -
Who cares how the string meets the turn of the worm?"

But then from the back of the crowd of onlookers
A small wispy voice hushed the sinners and hookers:
"My name is Twice Twister, from Hole-Under-Berm;
You must all heed my warning 'bout how turns the worm!"

The fiddle-dee dermed one, whose nose was unskint,
Found his smiling face freezing, somewhat set like flint;
The Twister's alarm gripped his ears like a germ,
With its repeated rubric of how turns the worm:

"The string should swing sweetly, inside of the post,
And go through the hole like a Z, not a ghost,
While the wraps should wrap downward, not curled like a perm,
So the gear, with less stress, teethes the turn of the worm."

"Therefore, the post should stand both firm and proud,
But nearest the nut," intoned Twice to the crowd,
More ingenious than Pratchett's famed Leonard of Quirm:
"The key must be headward to help turn the worm."

The flinty-faced fiddler, that seller of song
Of how it don't matter, that there was no "wrong,"
Responded, half-hissing, full-hoping he'd squirm,
While he twisted Twice Twister's turn-tale of the worm.

"Mister Twister," he said, "if what you say is true,
Then please explain why my way works like it do,
For it violates every Twice Twister term;
It simply don't matter which way turns the worm!"

Like a tennis match, back and forth, all day it went:
The Twisting of Twice Twister's calm argument.
But adamantine, like a rock he stood firm,
Awash in the current of how turns the worm.

Toward sundown, Twice Twister produced a necked box,
And proceeded to twist on some strings, in his socks;
As the twang tension mounted, the hookers did squirm,
For they'd intimate knowledge of the turn of the worm.

Then he handed it, tuned, to the treasonous one
Who, tempted by the crowd, tried to twist Twice for fun.
Twice silently motioned him notes to affirm,
Thus playfully testing his turn of the worm.

The fiddlestick four-flusher sourly complied
Wondering what trick might be hiding inside.
But the notes jangled tuneful, without any Sturm
Or Drang to destabilize Twice Twister's worm.

Abashed, he handed the box back to Twice,
Who proceeded to bend, hammer on, slide like ice.
The lesson thus learned, it was his turn to squirm,
As he choked on his diet of Twice Twisted worm.

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