I had always been told this never happened. I was a little skeptical, but since I never saw a sentence with two of the particle, I gradually came to accept that it was probably true.
Well ironically, in the DoBJG, where I'm pretty sure I've also read the above factoid, I've encountered this sentence:
この道を靴を履かずに歩けますか。
So I'm wondering if this is a mistake, or a weird exception, or if this "rule" I've heard is simply misleading or outright fallacious, and if so, when is it okay to use multiple wo particles in a sentence.
Cheers.