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Double Bass gut overall string length / alignment with nut

I build Ukuleles and DB is new to me but bought this at a Yard Sale

....so I have reset the neck on the 1937 kay bass and purchased Gut strings. In the Peg Head the holes in the tuner shaft is all to one side for loading each string. The Upton Bass tutorial for stringing shows a few wraps on each side of the hole and finishing rather straight in line with the nut slot. With Loading holes over to the side on this Kay Bass I only have room for one wrap before crossing to the other side of the string end. The gut strings by the time they have wrapped around they are no longer close to in line ... looking at the alignment with the nut slot the "A" and "D" strings are crossing over instead of looking straight in line.

So,I guess my questions are

1) how long should an unstrung Gut String be for a Kay Bass with a 41.5 Scale length?

2) what are the minimum no of wraps needed to not have string slippage on the posts

3) so if shortening the string is advisable to help keeping strings from a bad alignment What is the best way to cut Gut Strings
 
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Well, I don't pretend any expertise, (and, yes, that A string looks too short...) But if the D actually was "in line with the hole," as you suggested, they would definitely not be in danger of crossing. I am surprised that the A is that thick--- I guess I would have imagined that to have been the E...which of course does not need to be quite as long.
But there are lots of genuine experts here who can give you a better response.
 
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Ahhh thanks 1st ….sorry I didn’t yet wind the A string on….. I stopped because I didn’t like the projected location the string as it really is much longer and was decidedly too long …. I did continue stringing and cut about 4-5” off the length of them and still not completely happy but it does look better …. The E string is a bit heavier at 3.6mm and this A string is at 3.1 mm thick …. I’m just a bit out of my element and a bit cautious as I’m trying to learn about this instrument…. Thinking of finding a local shop to do a set-up so I will know it has been done correctly and then I will have a frame of reference to establish in my own head…..
 
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Yes the bass was made in 1937 and I thought the lowest tension would be best …. Also historically I would think gut would have been the original type strings … Since I know nothing about playing a upright I figured starting to play low tension also might be easier. I’m a guitar player ukulele builder and was just intrigued at having this Bass and bought it cheap in need of a neck reset….
 
For me, cutting a string on anything is almost a mortal sin, but I do something similar to what Jeff does, or at least achieve the same effect. I run the string through the tuner hole until I have about 1/2 to one inch through,
and then lay that along the tuning shaft towards the opposite cheek. I then begin winding at the loose end of the string, working back toward the hole. The winds anchor the loose end to prevent it pulling back toward the hole, and the final winds align pretty well with the nut.

I know this method puts a "hump" on the tuning shaft, but so far I have experienced no ill effects from that.
 
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It seems this Pistoy D I just got was cut a bit, it's definitely shorter than the Lyon D it replaced. The tail end is only about 2"-3" long and I just tucked it under the A string. The G tail is 6"-7" or so and I coiled it around itself and tucked it in between the G and E pegs (visible in the photo above.)