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how long is too long for a cable with passive electronics?

The response of a pickup+pots+cable+input is not flat with a rolloff on the highs that is cable dependent. The response has a peak that is dependent on the impedances of all of the above, and then rolls off. A longer cable could actually give more where you can use it while rolling off highs you don't need. You just have to experiment.
 
I play a passive P (Fender original 62 pup) and use a cable about 50 feet long for setup and sound check (so I can wander around the room and see what my rig sounds like from "out there"). I switch back to a 12 footer for the actual show cause we're a 7-piece band playing small stages - I have no room to move anyway and I hate standing on cables so may as well keep it short.

I honestly don't hear any difference, but I do play flats and roll the tone knob back about 1/3 of the way, so if there is any attenuation happening in the highs I probably wouldn't hear it anyway. Especially once the band is playing.

I made all the cables myself. I *think* the bulk cable was "Horizon" brand, (paid like 30 cents/foot), and I put fancy Neutrik plugs on the ends (each cable has one right angle, one straight). I put that "tech-flex" stuff (black of course) on the 12, 6 and 3 footers just for a little added durability.

So far so good....
 
Since Planet Waves has treated me so well, I would prefer to continue to give them my business. I'll probably just get the 20' and not stress too much. I tend to roll the tone knob back a bit anyway and I'm getting some replacement pups (Delano Jmvc) that have a slightly higher output as well compared to my fender CS 60s pups.
Does a higher output pup help combat signal loss?