Is the sentence grammatical?

Yes, it is grammatical, but very awkward.

Con beat me to it, Guat, but I might'a writ

Ambiguity can help people with diverse sets of opinions collaborate with each other (or w/ one another) or

Ambiguity can help people with diverse sets of opinions to collaborate

Or you can replace the "to" with a comma, but then it's kinda stiff-necked

Kinda fun; wish tho you'd prof

bold part mean?

Ambiguity can help people with diverse sets of opinions with collaborating with each other.

I believe the above sentence is not natural, but is it grammatical?

Thanks.