First off, my views mirror your views.

Literally just two days ago I had to make this exact decision myself. My current handset is stuck on 5.0.2 and will never receive another update and is a little buggy/restarts itself.

When I looked at the market the iPhone 7 is extremely compelling. At the same price point as the Pixel it simply offers an excellent value proposition, updates for 4 years, an OS that has improved a lot, top class hardware (inc. real waterproofing), best in class CPU, great camera, and aside from the lack of 3.5mm jack no obvious downsides.

I was legitimately evaluating going to the T-Mobile $30 prepay plan and then using the savings (pay $70 now) to do the Apple iPhone Upgrade Program. Ultimately after reading more about the T-Mobile $30 prepay plan I decided against it (no tethering, if you miss a payment they increase the rate, new customers only, etc).

So TL;DR: I wound up going Fi and Pixel ($20+$15 "plan" on Fi but with less downsides than T-Mobile's $30 prepay plan). I think the Pixel is worse than the iPhone 7 and too expensive, and I think all of the Pixel's features are gimmicks (VR) or will eventually ship on other handsets (assistant), but ultimately Fi is a great network and I didn't want the 6P/5X due to 12 months of updates remaining.