Apple

I started on the iPhone 3G. And while I've never owned an Android as a daily driver, I've certainly had to use them or support staff or customers at work who needed assistance doing something on them.

To me, iPhones are just about as easy as you'll find, yet still have a lot of capability.

Sure, modding the phone back in the day with Jailbreaking was cool and fun to do, but the iPhone kept adding features that I was getting through JB, so it just was no longer worth the hassle of not only going through the process, but then also not being able to update the phone with security fixes.

I like the quality of the build, the fact that the phone basically doesn't crash (I remember back in the 4 days, trying to run tons of apps at the same time, and the phone just wouldn't slow down enough to be noticeable), and of course the ecosystem is great - I got the iPad the year it came out, and only last year did I finally decide to get the Apple Watch, and that's been great for tracking my health in general, as well as being useful at work.