I don't wish it was simpler. It's tough to design complex technology that can satisfy both basic users and power users. I suppose Apple has had more success at doing just that than most companies. A smartwatch adds to the difficulty because the micro size seriously limits the amount of information that can be displayed at a single time, and also limits your input options.
There is definitely a learning curve, but the scale of that curve is partially determined by what you want to get out of the watch. The basics are mostly simple and intuitive. I still wouldn't recommend one for my 80-year-old mother. In fact I tried to talk her into sticking with a flip-phone and getting an iPad when she wanted an iOS device. She really wanted an iPhone, so we got her a basic model. She barely scratches the surface when it comes to what the device can do, but she has had fun learning. She loves seeing pictures of her grandchildren on Photostream, and she likes texting. I thought she'd prefer her iPad-mini but she uses her iPhone much more. She things my Apple Watch is cool, but not something she wants. My 5-year-old really wants an Apple Watch like her dad, and it took her very little time at all to figure out the basics. Regardless of age you will probably find it simple enough if you are really interested in using it and you have the dexterity to use such a small touch-screen interface.
I think of the Apple Watch as an accessory for power-iPhone users, but as long as someone has more fun with it than frustration they will probably really like it in the end. Five months ago I thought it would be a bit frustrating for some, but Watch OS updates (and app updates) have removed most of the frustrations early adopters experienced. It still takes a new watch wearer a week or two to get used to how everything works, but in my opinion most of that is just discovering features or tricks you weren't aware of in the beginning. I suppose it's also learning how to tweak things so you aren't over-notified... but the important thing is the fun-factor. My wife has no interest in the watch and couldn't understand why I wanted one, but after 10 minutes of playing with mine she said it was really fun and cool.
Sean