Maybe this helps you out. Yeah, I'm in a similar place. Have a MBP Retina that I love, a Windows 10 PC that I love, and a phone that needs to work with both. E.g. I use OneDrive for all my files but Mailbox for my email. I can upgrade in a month or two, and I might be able to get last-year iPhone for a price similar to an off-contract new Moto X. But I want a good battery in a small-ish size, so I'm also looking into the new Moto G ($230 and a killer battery). Cheap enough that I can just not insure it. But too cheap to be good? And I also need to combine it with a plan, somehow. #firstworldproblems
I am currently running a rooted, unlocked Nexus 6 and an unlocked, not-rooted-yet-because-Oneplus-is-a-pain OPO. The N6 is android; the OPO is a daily a couple days old because the rooting tools will convince you you're rooted, and you're not, and then you attempt to install Oxygen and you soft-brick. I ditched the 4S a year ago. I'll never go back. iOS is shit. Yeah, it works all the time and yeah - you never have to fuck around in the command line via ADB and recovery mode just to get a dialer that will actually connect to your cell tower but these two phones combined cost less than a six plus.