Really you shouldn't change any adjustments on your bass when switching strings until you have actually switched the strings. I have never played Joe Osborn flats but I have heard that they are fairly low in tension by comparison with most flatwounds. I have a bass strung with Thomastik flats and they are the lowest tension strings I have ever played.
In most cases when switching from rounds to a similar gage set of flats, tension will increase, and a tightening of the truss rod will be needed to maintain the same amount of relief in the neck as before. But when first using the Thomastiks, I actually had to loosen the truss rod, in order to maintain a bit of relief. So, I would not advise you to adjust your truss rod first, unless you are certain that the tension of the new strings will be significantly greater or lesser than it is now.
I would also think that, as with the truss rod, you cannot really make pre-emptive saddle adjustments for string height and intonation, before actually stringing up with the new strings.
It's interesting too that different makes of strings of similar gages can significantly vary in tension, and resulting feel. I recently tried a set of Ken Smith Burner Nickle-Plated rounds in 40-100 that I had thought might be lower in tension than I am used to with 45-105 D'Addarios, but the tension stayed about the same, as did the neck relief. Surprisingly nice strings, these Smiths. I never would have tried them, had I not seen a new set for sale at a garage sale....$5....great grab. Good deal at the regular price too......
http://www.juststrings.com/ksb-aa-bbl.html
Also, as far as using flatwounds on a bass with a string-through-body bridge, I would say to go for it. I own a Travis Bean bass that is a string-through bridge and have had Ernie Ball and LaBella flats on it with no problems.....oddly enough, I have never broken a string of any kind on this bass.

