An interesting thing that we forget with Bob and Clippy is the people reviewing/commenting on it are almost by definition NOT the people it was aimed at. Having sold 58k copies, there must be some people who actually used it.
It never replaced the actual desktop, but it was fun to go into my own 'house' on the family computer customized to my liking in the days before profiles and separate logins.
It was an interesting idea. I get the OP's point that a lot of the critics were not the target audience, but for the most part the target audience didn't take to it either. I guess I don't see that as a preordained conclusion, and I don't think of Bob as an obviously bad idea from the start, it was just one of the many new ideas PC developers were trying in the mid-90s as computers were rapidly expanding their reach.
My parents were deep involved in a franchise of computer learning centers for kids in the 90s, so we wound up evaluating a number of them over the years. Probably the most successful and one we used the most was KidDesk. Bob came out right at the end of that era (near the end of the business) and there was a lot of interesting hope for it. The business bought a bunch of copies (at a steep Microsoft Education partner discount, IIRC) and had high hopes for it as a "starter desktop"/teaching tool. It had good ideas from that perspective, and if they technically solved a few more "launcher" problems like Windows 3.1 transition to DOS full screen app then back (which KidDesk had a hacky version of) it might have filled some key niches if it had launched 3 or 4 years earlier.
Ironically, I think the real thing that killed Bob was Windows 95, even for the users that were the target audience. Windows 95 fixed a lot of those Windows 3.1/DOS transition states, was much easier to teach and generally more kid/family-friendly, and there was a lot less need for an "alternative" desktop.
(My experience with Bob makes me sad that the Cliff House for Windows MR still is too chilly and cold and "professional" and needs Rover or Links walking around and/or offering advice.)
[1] And not even really the last when you look at for instance what's going on with "Kid versions" of Amazon Tablets as one extension of the legacy. Or the continued explorations of virtual agents in Siri/Google Assistant/Alexa/Cortana as another fork in the evolutionary tree.
While Xerox and Mac helped shape the current "desktop metaphor" GUI it was still an open question how to migrate those used to DOS-style command line tooling to a GUI, and it wasn't really "solved" until Windows 95 (where the Start Menu became "Bob" in a way).
We're probably always going to fight skeumorphism debates on where the right balance is for user ease of learning/discovery ("I know what a typewriter is, if I click can I type a document?") versus the density compaction (both in physical space and arguably in mental space) of reducing "skeumorphic clutter". (The typewriter in Bob was thousands of pixels to display even its simplified cartoonish form; the [W] logo of Word fits as small as dozens of pixels. Similarly too, once you know Word exists does "I need Word, and its a word processing app, so I should think of a typewriter and click the typewriter" get in the way of "use Word"?)
Other examples I included even in my above comment. Whoever "Bob" was, his home/office made him seem a curious luddite or eccentric throwback. He used what seemed a 1930s typewriter and his style of rolodex was from at least the 1950s, IIRC. On the one hand it was kind of cozy like visiting the home of a loving grandparent (perhaps Bob was always meant to evoke everyone's collective eccentric grandpa?), but on the other hand there was some "ludic dissonance" in that it was supposed to be "your house" and you were encouraged to customize and play with it. Why would I keep a typewriter so prominently? Are we sure we want a massive metal rolodex that's more likely to injure people (if not also be a tetanus risk) than be useful in a house with (talking) pets? Bob's skeumorphism was already dated in the 1990s that it launched into, and that's a fascinating reflection of it as well.
I thought it was the coolest thing ever.
I also remember an encyclopedia program that was wrapped in a virtual spaceship interface. For a bit, I just thought that these sort of graphical interfaces were what computing was.
It was kinda fun, even though it wasn't really a game.