I used to have an iphone, then I switched to Windows Phone for a couple of years (the app store was pretty barren but it was fine in terms of basic functionality) and now I've had an android phone for the last ~3 years or so. I am probably going to get the new iPhone when it comes out because my job offers better IOS email access than through Android, and I want to take advantage of that.
There's never been a huge adjustment for me, and all were usable. Each has their positive and negative quirks. If I had to rank them I would go:
Android: Probably my favorite just because of the number of phone options and software tweaks you can do. Fine as an OS. That being said, a lot of phone manufacturers (Samsung I am DEFINITELY looking at you) put extra crap on top of the base OS that offers no value but makes it worse to use, displacing good default apps with crappy custom versions. This can be fixed but is a pain. In addition there's just a higher level of jank with Android, because it's a more open system and there's more variety in hardware. IOS runs pretty smoothly IMO but Android has more errors and issues to get around. Finally, and this is true for all the systems, as you keep your version of Android upgraded your phone gets worse and worse. My battery life is terrible now and I replaced the battery like a year ago. It's a combination of adding new power draining features and trying to push you to upgrade your phone.
IOS: This is a smoother, cleaner, experience than Android but also much more limited in terms of customizability. You also are much more limited in hardware choices. It feels kind of sterile in comparison to Android and Apple puts more controls and limitations on your experiences, but it can be nice not to worry about jank. It's a bit like the PC vs Console experience in comparison to Android. If you still use local music (as opposed to streaming) on your phone then iTunes is complete crap at this point (it used to be so much better in comparison to the competition) and iPhones charge a ridiculous amount for extra storage space (my Android phone let me slot in a 128gb SD card.) Like with Android, Apple will try to force you to upgrade through OS upgrades that make your phone slower and (especially) have lower battery life.
Windows Phone: It works for basic functions but doesn't get the big games or the moderately popular apps (it does get the biggest apps). It's fine for someone who just wants to call, text, search the web, email and have a GPS. I didn't hate using a Windows Phone, but it's impossible to recommend.
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