I also had WM phones at the time of the iPhone release. Most WM users at the time, myself included, were power-users who criticized the iPhone for a lack of features and never actually bought one. I couldn't install my network scanning app, connect to exchange, or even copy/paste with the iPhone, so what was the point?
Turns out I was entirely wrong: Apple wasn't positioning this phone for IT/business professionals for corporate use. They were building a consumer product. The feature set they were prioritizing was entirely counter-intuitive from my perspective. The features that I thought were gimmicks at the time ended up being the features that made it successful: natural multi-touch input, a (then) gigantic screen, and a bare-bones UI/UX. It had nothing that I wanted or needed, but it had everything that they needed to open up the market to millions of people who weren't using HTC bricks on their Verizon corporate plan that their IT admin configured for them.
Just search "windows mobile" on YouTube and look back at the awful (but feature filled!) experiences we used to think was awesome. For example: https://www.youtube.com/watch?v=PXDgsZvSTP8