Every time I go to upgrade some piece of electronic something or another, I feel exactly the same way. Currently going through that with our smart phones. We have 2: a Blackberry that I love, and an Android that I'm not very fond of.
All are friends are telling us to go to an IPhone, but I'm doing my research and checking out all the phones--not to mention all the carriers and their plans.
TL; DR: Get an iPhone with 32gb or more. If you need a data plan, make sure you get a big enough one!
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I work for a company with approximately 20,000 users. We have 90% iPhone and 10% Android. Allegedly, 90% of the calls for phone
troubleshooting come from the Android users. So, take that for what it's worth. We have maybe a half dozen Windows Phones and Blackberries. These are so unpopular, I'd never get one.
If you don't mind a slightly wonky white iPhone 5c -- the very top of the display has white image defects, but otherwise works OK -- I can send you it, but you'd have to get your own service, of course
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I have an iPhone 5S as my work phone. That's two models ago, but still runs the current iOS software (9.1). While I don't particularly like the layout of the Podcast app, I do like the fact that I can press a button and tell Siri to do something and she generally does it right. I haven't even tried the Google digital assistant, which is essentially the voice control on the Android phones, but can also be used on the Mac. That might be interesting.
My opinion on Android phones is that you should get either a Samsung, because they make almost everyone's cell phone guts, or what's specifically
mentioned on Google's Phones page. The Google-authorized phones and tablets are generally (always) called "Nexus" and generally have a couple numbers or letters after that. These should be the most compatible with the current version of Android -- called "Marshmallow" or 6.0 -- and will probably do just fine with Android 7 and 8 when those come out. After that, it's more or less your preferences: do you want a really big screen? Sharper screen? Better camera? Fingerprint scanner? Etc.
I do recommend that you get at least 32gb storage. Just the operating system and the built-in apps will total almost 16gb. Data plan? I really don't use my phone for web browsing much, but I do use the GPS quite often. My usage is currently at 8.2gb this month. I do have an unlimited/unlimited plan through work. I'm fairly sure it's $140 a month. We also have the "warranty" where if the phone breaks, you get another of the same make/model. There is a sensor in iPhones that will trip if it's dunked in water, so that's not covered. My wife, who doesn't work where I do and has a different cell provider, has some breakage protection plan, and can get a new phone after 2 or so years. My daughter got an iPhone 6 from her grandparents and broke it. She's going to have to get the screen replaced because there's no breakage plan. That's about $100. Yes, I could replace it myself for a lot less, but I don't want to. Those screws are really, really small.
FWIW, I hate the phone call quality on ALL smartphones. When I had a Motorola flip phone several years ago, it was an awful lot clearer and an awful lot cheaper than my iPhone.