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5 string set for 33.5 scale bass

Can you post photos of the headstock and how the B string is wound? Half an inch difference shouldn't be causing strings to break with any regularity. I've done all sorts of dumb stuff in my youth with B strings and they very very rarely actually broke.
These are exactly my thoughts. It's not the half an inch difference, there's another factor to the B string breaking. Possibly the angle from the nut to the post. Possible what this bass actually needs is a string tree specifically for the B.
 
It breaks when the full string radius hits the tuner post.
Then ruling out any possibility of a missed burr, what length are you leaving the previously broken strings when you insert the end into the saf t post? Typically one should leave two full posts worth of length past the post being used but there’s nothing wrong with keeping more winds if they help.
Assuming it’s the tight bend radius splitting the full thickness outer winding on you, try just leaving more wraps so once the thicker part of the string arrives it’s touching the thinner parts of itself instead of the post. Two wraps of the thin part of the string will nestle the full size atop them and ease the bend radius.
 
It breaks when the full string radius hits the tuner post.

I have some medium scale basses with full scale strings, and even the lowB that occasionally wraps more than once around the post, without breaking. So it may be down to technique of how you wrap the string.

The advice I got, and has worked for me, was to pre-bend the string around the post before it gets tensioned (by hand), before using the tuning key.

This way the core gets gradually bent, and doesn't seem to stress as much when the string is finally tensioned using the tuning key. I believe I have a set of Daddario xls installed like this, intact.

If that doesn't work, then adding spacers or bushings at the outside of the bridge would be my next go to solution.
 
fretnation.com has the short-scale 5-string sets by DR and by Dunlop. I can't remember which one works with my string-through short-scale (DR?), but maybe that would be long enough for your bass. Worth checking out, at least.
DR "short-scale" strings are indeed longer than most, and there are 5-string sets, but they're under 34" winding length, i.e. a good option for many 30"-ish scale string-thru-body instruments and 32" toploading ones, but not the OP's.
As for Dunlop, in one of my posts above I mentioned a set by them (DBSBN45125M = Dunlop Bass Strings Super Bright Nickel 45-105 Medium-scale), but it also may be too short for the OP, even accounting for some eventual stretching of the strings, and it doesn't appear to be currently in production: the only four medium-scale products (two 4-string ad two 5-string sets) shown on the website are flatwound.
 
Just to reiterate, whatever problem OP is having is 100% not an issue with the strings themselves. I know it's fun to give string advice but a bass with a very slightly shorter VSL isn't going to cause B strings to break with any sort of regularity even if wound around the post haphazardly.

This has been debated a million times. Some people have problems, some don't, and it probably depends on the string, the bass, the tuners, etc., etc., but it can be a problem if the non-tapered part of the string winds onto the tuner. I've seen several people allow their B string to "bow" between the tuner and the nut, and they probably didn't have a problem, but I bend it straight, and I have had a problem. I bet there is a string that fits correctly, so why not?
 
DR "short-scale" strings are indeed longer than most, and there are 5-string sets, but they're under 34" winding length, i.e. a good option for many 30"-ish scale string-thru-body instruments and 32" toploading ones, but not the OP's.
As for Dunlop, in one of my posts above I mentioned a set by them (DBSBN45125M = Dunlop Bass Strings Super Bright Nickel 45-105 Medium-scale), but it also may be too short for the OP, even accounting for some eventual stretching of the strings, and it doesn't appear to be currently in production: the only four medium-scale products (two 4-string ad two 5-string sets) shown on the website are flatwound.

Yeah, strings for 32" medium scale are usually right for string-thru 30" basses, so any string for short-scale would be too short I suppose.

Yeah the short-scale DRs are 33.75" winding.
 
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Yeah, strings for 32" medium scale are usually right for string-thru 30" basses, so any string for short-scale would be too short I suppose.

Yeah the short-scale DRs are 33.75" winding.
Actually, for a year-ish DR has been making the E string in their "short-scale" sets even shorter than that, namely 33", as reported here and =16&c[user][0]=237573']here, and that may well apply to their shorty B strings as well
(which, if true, would make it even less applicable to the OP's bass, which is 34.68" ball to nut).
 

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