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something something "I'm a frayed knot" and "arrrr it's driving me nuts".

Probably should be read through a lens of "dry sense of humor mixed with word play." Helps if you know anything about "working in IT" memes.

My problem is that if there was a two bear minimum, he'd let in more bears

I think it means you should have shown up with another bear.

And maybe is commentary on how a statement can be interpreted in two opposing ways, serving as a monkey wrench in the gears at times.

Don't you fulfill the bear minimum for understanding this pun? Try frequenting lower bars.