I had every single C&H book growing up. I wish he'd draw again... maybe they can teach him how to make a webcomic? No confining panel structure here...
From what I've heard, dude is basically kinda done with the comics grind.
Which is not surprising. I do a webcomic, and have no day job to distract me from it, and yet sometimes I can't even manage one page a week, let alone the six B&W strips and one Sunday strip that being a Syndicated Cartoonist involves. I have a friend who's doing the syndicate gig right now[1] and she's basically impossible to get ahold of because she's always got to stay on top of her buffer.
It's kinda like coding for video games. It's a dream job but the reality is that there are a ton of other people clawing for the same position so you better work your ass off, kiddo!!11!!!. Well, okay, maybe less of a dream job now that newspapers are dead but you know what I mean. That shit burns you out but good.
I am sure there are pretty tough pressures on your friend, or any other SC. I am sure there are lot of others to replace them.
But this man is not a SC. He is Bill Waterson. If he wants to have a panel once a week, in full color, only on thursdays any newspaper editor who turns him down is an idiot.
As for making him a web cartoon artist, all you need would be hosting somewhere, a server that can handle the traffic and one message to whomever moderate the Facebook Calvin and Hobbes Fan group, plus a twitter account that sends a message each time a new cartoon is published.
Your ingredients list for getting Watterson on the web is missing one important thing: him wanting to start showing his work to the public again.
Who knows? Maybe this little thing he did with Pastis was him testing the waters. He might have been asking himself "Do I still have it? Do I still WANT to have it?" by drawing these. Maybe he's toying with some sort of return. Maybe he's about to drop some awesome personal graphic novel that's been brewing this 20-year-sabbatical. I know damn well Universal/Gocomics would kill to set up a new presence for him on pretty much any terms he wants. Half the web cartoonists he met via showing up on Stripped! would probably do it for free.
But does he want it again?
I mean, he retired into aggressive anonymity for twenty years. He might have recharged. He might still be completely burnt out.
We can't know. And that's entirely what it rests upon.
Yeah, but that's the thing. With a web comic he can do whatever he wants. Pure freedom. What he wants, when he wants. Hundreds of people would pretty much work out all the details for him just to put it on a page somewhere, I would imagine. And it's not like he'd have to come out of hiding, either. The web pretty much allows you to do as you like in that regard as well.
Sure, it's just wishful thinking, but it wouldn't be that hard to give him an outlet to do as he pleases, assuming he wants to do something.
Yeah, but Watterson clearly doesn't like working with technology. He's very much a pen-paper-human kind of guy, and I don't see him all of a sudden deciding to step into the internet.
I'll be darned if he couldn't find someone to work with who could handle getting his work online though. It's mere wishful thinking, but he could draw and communicate (or not) in whichever way he wants, and some trusted friend and gatekeeper handles all of the scanning and online stuff, which could be kept very simple and noncommercial. No ads, twitter, comments section or any of the usual "social media branding" stuff, literally just a page with a comic on it.
Judging from what some other webcomics do, it would be beautiful. This webcomic shows how much freedom can be had with paneling, and how detailed the art can be: http://dresdencodak.com/2010/07/10/dark-science-03/
