One of the concerns I have, and I believe Steve shared, is the dilution of their offerings. I'm frankly having a hard time navigating their iPad and Mac offerings. It isn't clear where each of their products sit, and it's certainly going to be very confusing to non-enthusiasts who have the grit to swim thru it all. Similarly, someone explain the 13in Macbook Pro? Why is it still here and getting updates? It seems to me that they are just making all possible combinations of their products, and Steve hated that.
I'm with you on that, but it's very far from how bad it could be - just take a look at the other computer manufacturers.
And the trend of making the product lineup more convoluted doesn't seem to be steep (it happens slowly and over time), so I'm not too worried. It seems there is time to steer it back before it gets too ridiculous.
It seems to be mostly a case of, as various product sets evolve, you sometimes end up with adjacent products that are probably too similar. This has happened with the MacBook Air and MacBook Pro at various times. In general, Apple seems a lot more guilty of being slow to upgrade niche segments (smaller laptops, high-end desktops, smaller phones) than the other way around.