Am I wrong to worry about real life interfering with OotS? Is it "entitlement?"

[KorvinStarmast]

There's a sense of investment that I don't feel with reading any trade comics, books, tv shows, etc.

It's a comic book that you read on the internet.

Maybe Rich wins the lottery or becomes lead developer of next DnD edition

Bad idea.

I wonder if it could just suddenly stop one day and we would never know anything else about these characters and to what ends their adventure was taking them.

Easy to do. It's a comic book. But I, being a selfish old fart, sincerely hope that this does not come to pass. I want Rich to live At Least as long as it takes him to finish the story, and to write another story about something else, and even longer than that. He's grown as a writer, before our very eyes, and I'd love to see him do a book or a graphic novel that had nothing to do with D&D.
That would be cool.
But if it does not happen my life goes on. But selfish me wants more of his stories.

Of course, real life being what it is, nothing is absolutely safe. Any show or periodical you have been following for years can stop suddenly for whatever reason,

Shows and comic books are the decorations of life. Life itself is the dinner party.

My question here is, is it wrong for me to be wondering if there are some contingency plans in place to take care of the long time readers of the comic?

I'd suggest you check your priorities.

Picking someone else to continue your work is often a bad idea. Look at George Lucas. (Yes, I wanted to be the first to mention Star Wars in this thread)

He made a mess of his own idea: Jar Jar Binks, for just one example.

I don't know anything about the person behind the alias of "The Giant", so I can't say anything useful

He's from Philly. That's not a good thing. But he's the author of OoTS. That's a good thing, squared. On that balance, good-thingness seems to win.