Don't feel bad I thought the same thing, I almost suggested he change his avatar from Cobra Commander to a transformer.

Size doesn't matter? Yeah, sure... ^.^

Well, size does matter and your comparison is flawed because you're only using one side to make that comparison. The GameBoy could be less wide, but it was also much thicker, allowing our hands to hold it easier. And the SNES was not only 1 inch wider, which is a lot in this case, but (looking at pictures) it's also taller and rounder around the edges, again making it easier to hold.

I hate the name Joy-Con ... if that means anything ...

Just reminds me of the old Playstation one controller

https://en.wikipedia.org/wiki/Jogcon

If you ever used one of these things, was awful.

Nope, never saw that, but it does make me remember a one handed controler I had for either PS1 or PS2 (that thing has to be in my house somewhere) it was for playing RPG's mostly and I forgot how much i liked it. 

From what I can tell of the videos, they do look rather uncomfortable when playing more so when playing with a friend. It seems more of a gimmick to me.

Yes, but the face buttons an d-pad were on the side, not in the center.  Try holding an NES controller and hold either your left hand or right hand in the center rather than the edge, and press buttons.  This is the bigger problem than the size.

And no N64 is not a counter example.  That had a center grip.

Next take a Xbone or PS4 and try controlling as if stick were directly under the buttons.  That shows the problems with the grip controller.

It's not hard to test the comfort in either scenario.

So joy-cons and grip controller will both be unsatisfactory control options, so again, what is the point?  I guess stand alone tablet could be useful if it is fully functional.  I have my doubts Nintendo could pull of a workable UI.  

Also, Wii mote style functionality could be useful as well.  I'd be interested to understand the mechanics of how that would work on go and home (what replaces the sensor bar in both cases)?

If they have motion features in them, then having smaller joycon controllers is a lot better.