I will say Steve would for sure be happy that Apple has become a cash cow over the years. But after reading many books about the guy including his official bio, the Watch would either never have come out....or came out a couple years later than it did. It was purely an unfinished product that Apple had NO IDEA about how to present to the market. Steve was always crystal clear on a products vision and intent. Also he sure as hell would have sold and marketed an $1100+ iPhone (Excess MAX) a lot better to people.....and not have given it that ridiculous name.
Take a look at my post above. The Watch was a Steve product, but it had (and still has) a far different purpose than we see. Right now, they're building all sorts of tech into that device in order to get it on as many people's wrists as possible. At a future date, its going to interact with HomeKit, and with MacOS/iOS, in ways you wouldn't believe. When you see it happening, you're going to know who conceived of it.
The names are definitely getting ridiculous. I really don't know how to solve it now. I was upset when Apple started phasing out "i" names for products, but in hindsight I didn't really see how fatiguing it was becoming. It didn't help that outside products were accumulating iNames as well. I'm glad we still have products named "iMac" and "iPhone", but it would have been ridiculous to see an "iWatch". I think the most ridiculous was "iDVD", and I think even Steve saw that was a name too far.
Kind of sorry that iMessage is now just "Messages", though...
The downside to dropping the "i" is now Apple has become a bit more like Microsoft, with "Apple" preceding the product name just as everything MS used to make had "Microsoft" before the name. Microsoft Word. Microsoft Excel. Microsoft Access. Branding is great, but it can become oppressive. The lowercase "i" was a great brand for its time, and Apple neatly avoided MS naming convention by using it. But it couldn't last forever.
So what should be done about the naming? Far too many things in life are getting defined by nonsense strings. Cars used to be known by simple names, usually totemic. Cars were named after animals, winds/storms/other forces of nature, or places. Then some genius said "Americans like numbers more than names", and yes that was an actual article in a national media outlet back in the 80s. Ford had changed the Escort to the "EXP" and imported a model from Germany and called it the "Merkur XR4ti". Other manufacturers had already started making models out of what used to be option codes. The Z/28 stands out. BMW recently made cars called the Z4 3.0 s-drive, and I think in current years the numbers and letters have gotten longer.
The point here is that we're practically using SKU numbers to refer to things now. People will have to be able to read and speak UPC and QR codes in order to talk about products. The rest of the cell phone market has already swung that way, and Apple is not far behind. I'd venture to say we're in for a naming shakeup, and I hope Apple leads it.