Reads as nice memories of a memorable character who was a part of the evolution of our industry. I enjoyed it.

Seemed to me like a nice write up with a bunch of anecdotes, I got the sense that Bob was curious, friendly, smart, maybe hopped around from idea to idea(reminds me of me!), and generally lived a good life, made some things(the YouTube video seemed interesting).

Cringely was a character. I can't say he changed the world in a major way - he was no Bill Gates or Steve Jobs. Heck, he wasn't even Eric Schmidt. But he was a clever, charming, and interesting person, and his coverage of the tech industry made it feel a lot more glamorous that it really was. He was also a fabulist and possibly even a bit of a scoundrel. That said, I do think our industry was better with him in it.

Depends if you think he should be damned for such minor sins. I have dead people who have done much worse who I miss like crazy, and still laugh (and get sad) when remembering some of the worst things they did.

I find Plane Crazy really charming, although it's a portrait of someone who I definitely wouldn't do business with.

I also find it endearing that the OP thinks that he'd have been just as good as the modal successful startup CEO if one of his ideas had accidentally hit (despite him.) I agree. There are a lot of Cringelys running massive companies, but without the heart that he had. The man seemed an often self-destructive dreamer, but not evil in any way as far as I can tell. He seems to have honestly liked people, and to be driven by wanting to impress them through making their lives better.

Yeah, frankly the guy seemed like a real cad. I've always recognized the name as someone who was "around" the tech world, but never was clear to me he did or said anything interesting. This does not dispel that impression.