Apple collaborated with Motorola on an iTunes phone, which was very much ill-fated.

I remember seeing it before launch at a rooftop party in Chicago. The Motorola engineer said “it’s going to suck, Apple made us cripple it”.

Apple learned; I guess FB gave up.

Exactly the point. Many people will lesser vision would have given up at the Motorola Rokr too and just focus on iPod.

The lesson wasn’t “this doesn’t work” the lesson was “we need to control this completely for it to work”

Also for a laugh watch Jobs demoing the Rokr on stage, you’ll see him visibly get frustrated with the UI. IIRC.

I think that one major difference is that the iPhone supported an "easy" way to do software updates, which was never a thing prior to smartphones.

Remember that the iPhone wasn't really that good at launch, either. No copy/paste, no App Store, etc. There is a scene in the movie Sex and the City, which was filmed pre-launch (right?). One character hands an iPhone to the other, who looks at it for a few seconds and says something along the lines of "I don't know how to use this" and hands it back.