So, I visited an Apple Store for the first time in my life over the weekend. I'll have to admit that it felt icky when I first walked in, but that all went away rather quickly once I started talking with one of the salespeople.
After spending a long time playing with the devices and asking questions, I have decided that I am going to leave Windows Phone for the iPhone 6. There are a few things that I will miss about WP, but none of them are deal-breakers. The main thing is Cortana. She really is that much better than Siri. The other thing that I found that I will miss is the People Hub. Microsoft has done a really good job with that part of the OS. Unfortunately, the way things have been progressing over the years, I would expect to see them abandon the People Hub in the near future anyway. It's really one of the last remaining features that really set this operating system apart when I picked up my first Windows Phone back in 2010 and I'm afraid it will go the way of the Me tile, and the old Photos Hub. It's a shame, really.
So anyway, thanks to everyone who helped out with my questions. Microsoft services-wise, this will be a very smooth transition. And you know that feeling of disappointment that every WP user has pre-loaded into their gut -- you know, those nagging questions: "Will that new app/home automation device/web cam, etc. be available for WP?", "What is the next app that's going to pull support from the platform?", "Will my phone get the latest update?", "Will the next flagship be available on my carrier?", "Next year, things will be better, right?" That feeling is gone now and it feels pretty good.