I’m Not a Mac #17–The Agony and the Agony of My iPad Pro

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This post is part of my “I’m Not a Mac” series, chronicling my migration away from Apple after many years as a Mac user–and my journey back again. Find other entries in the “I’m Not a Mac” series archive.

It’s been 18 months since I purchased my first-generation iPad Pro 12.9″ and sold my MacBook to go all-in with iOS. I thought I’d be cruising using a single operating system across all my devices. Instead, I often feel like I have to get out and push.

Prologue warning…

I’m not a person who claims platform sides. Mac or Wintel, iOS or Android, I like to use what works. Usually for me what work’s best is Apple products, but that’s not always the case at all. As I’ve chronicled throughout this multi-year blog series, I’m a longtime Apple user who also spent a long time away. I used Macs–lots of Macs (according to my Mac-geek spreadsheet, 5 desktops and 9 laptops in total)–for almost 14 years. Apple’s high costs and walled-garden ecosystem eventually drove me to a five-year stint in the Android and Windows worlds, which had its own pleasures (I fell in love with the Google cloud) and pains (I fell in hate with underpowered netbooks.)

Chance brought me back to the Apple fold two years ago, and the more lenient Apple walled garden of 2015 was a good fit. I bought a MacBook Air and Ryan and I quickly became a two-iPhone, two-iPad, and eventually Apple TV family. It wasn’t perfect but I wasn’t looking for perfect, either. I’m only ever looking for my computing devices and their supporting ecosystems simply to work as promised.

It’s a politically incorrect thing in Apple circles to suggest that things worked as promised a lot more under the late, visionary Steve Jobs than under the terrified-of-an-audience operations nerd that is Tim Cook. Trouble is, the suggestion, itself, is right on. I quickly caught on to that when I got back to the Apple side of things and realized that the tight product matrix I had walked away from had become a bloated, Dell-like, supply-side nightmare of flavor-of-the-month desktop, laptop, and mobile-device options that didn’t clearly line up anymore. That the innovations people were craving and using in the Android and Windows worlds–like touch screens on laptops, track pads on tablets, OLED screens on phones–were nowhere to be found chez Apple. And that feeble catch-up attempts wigth Android and Windows were now marketed as innovation. (iPads with keyboards and stylii? MacBooks with touch strips? iPhone displays that finally bother to break five inches?)

But everything wasn’t perfect on the other side of the wall, either, so I decided to give things time. Here’s how that has worked out over the past year and half that I’ve been an exlusive iOS user for work and play…

My work and play was slowed down for the first 15 months–until the iOS 11 beta and eventual final release gave the iPad a Mac-like dock and multitasking pane–by a half-baked multitasking procedure requiring me to scroll through an undless list of apps hoping to find the one I wanted to use in Split View or Slide Over.

My work and play was slowed down for most of this year by a series of iOS 10 updates that damaged the Bluetooth connection between my iPad Pro and my Apple Pencil–one of the two main accessories that make an iPad Pro and iPad Pro, turning what had been the best virtual handwriting and drawing I’d ever experienced into a nightmare of dropped characters, ghost lines, and illegibility. I was far from the only person with this problem.

My work and play was slowed down for the past three months by my iPad Pro intermittently rejecting my Apple Smart Keyboard–the other main accessory that makes an iPad Pro and iPad Pro, requiring lots of unexpected time detaching, re-attaching, and rebooting trying to get it to work, until Apple finally replaced my keyboard under an unpublicized quality replacement program because, again, I was far from the only person with this problem.

My work and play was slowed down on all my iOS devices by Siri and Apple’s dictation engine in general rarely, if ever, correctly understanding all–and sometimes any–of what I said to it. Not using the “Hey Siri” hotword combination. Not using dictation via the virtual keyboard. Not using third-party apps to record my dictation and run it later through Apple’s dictation engine. This was a big one–having to constantly correct every text response I dictated, every web search I tried to perform by voice, every blog post I tried to produce quickly without a keyboard was maddening. It still is. It drove me to replace Siri with the Google Assistant app on my iPhone 7 Plus and the Google app on all my iOS devices. Because of Siri’s suckiness, I also replaced Apple’s built-in virtual keyboards with Google’s Gboard, which offers access to Google’s infinitely more advanced dictation engine.

And my work and play was stopped in its tracks many times simply by Apple’s painfully outdated core email and calendaring software (cough SiriShouldBeIncludedHere cough) that aren’t even on par with the feature sets competing third-party apps had two years ago (and in some cases, much longer.) Until, as I recently blogged, I replaced them, too, with the far more feature-laden Inbox By Gmail and Google Calendar, and their amazing shared secret sauce of Google Reminders.

Still, after all my previous back and forth among platforms and OSes, I wanted to make it work. I mean, if you’re not going to try to like and work with the computing platforms and OSes that you, yourself, choose to spend your time in, then why did you choose them in the first place? Far all its (and really, Tim Cook’s) faults, Apple’s ecosystem is still amazingly convenient and incredibly coordinated among Apple devices. And since Windows on phones tanked, and especially since Google is concentrating now on Chromebooks with access to the Google Play Store instead of extending Android into a true multitasking mobile OS for tablets, being an Apple user is the only way to access the convenience and coordination of choosing to live in a single OS across all your devices.

On the other hand, after all that back and forth to find what works, I like to know what my options are. So while I’ve been sitting on my hands in please-work, why-don’t-you-work iOS land, I’ve kept myself apprised of the way things could be if I ever defected again to the other side–er, sides. I mean, love my iPhone 7 Plus and think it’s the best phone I’ve ever used on any platform. (I also think it’s beautiful and use my Rose Gold beauty without a case, but that’s a whole other blog post…) But I also loved the feel and enormous screen of my old Android LG G3 and the suaveness of Samsung’s Android overlay on my previous Note 4. I love the new multitasking features in iOS 11 on my iPad Pro. But I also loved the ease-of-use of Windows 7, 8, and 10–and those OSes didn’t demand that I give up a track pad. So throughout the past 18 months, I’ve kept abreast of the flagship Android phones and Windows tablets of the moment.

That still wasn’t anything more than wistful thinking until iOS 11 broke my iPad’s connection with my brand-new replacement Apple Smart Keyboard, with the only working fix to constantly reboot my device. Yes, twice in one year and across two different versions of iOS, the keyboard Apple designed specifically for my iPad Pro to make it an iPad Pro–and which has been on the market for nearly two solid years–stopped working with my iPad Pro because Apple can’t get a handle on the relationship between its current hardware and software. And yet again, I’m far from the only person with this problem.

So I decided to spend yesterday afternoon on North Michigan Avenue, Chicago’s high-end downtown retail district, window shopping for other options. I looked at Surface Pros at the Microsoft Store, Android phones at the Verizon store, and just for shits and giggle, the new, smaller iPad Pro 10.5 at Apple Store.

I saved Apple for last and checked out the other options first. I loved (absolutely loved) the keyboard and trackpad on Microsoft’s 2017 Surface Pros, as well as the form factor and the better way the keyboard and kickstand are design engineered versus the somewhat flimsy design of Apple’s keyboard (that I still could barely get to work with my iPad Pro.) I loved even more the feel and display of Google’s brand-new Pixel XL 2, as well as LG’s flagship Android phones (the G6 and V30.)

I’d heard about how the smaller iPad Pro 10.5 feels like the “golden mean” of iPads–not too big, not too small, not too heavy, but just right for working and playing in a size far more portable than my 2.3-pounds-with-the-keyboard 12.9″ model. I could see upgrading to the device six months from now when my device agreement is paid off. If only I had faith in my ability to actually use it, since I’d have to use a smaller version of the same damned keyboard that won’t work for me now.

I headed to Water Tower Place to sit in a Starbucks and take my mind off things by blogging. It took five minutes and two reboots to get my keyboard to work with my iPad Pro. Instead of blogging, I entered a chat with Apple Support. Since I have AppleCare on my device, I thought maybe, just maybe, it might be a hardware issue on the iPad side off things that could be fixed by a repair or replacement.

Instead, the Apple Support rep wanted to run me through all the same mindless, read-off-a-script things I had to run through before just to end up with a non working keyboard replacement. Yes, I’ve rebooted–it’s the only thing that temporarily solves things. Yes, I’m running the latest version iOS. Yes, everything is backed up, and I’m down the street from the Apple Store. And then…

No. I am not spending the next eight hours factory-resetting my iPad Pro, reinstalling every OS update, reinstalling all of my apps from backups, and re-entering every single one of my settings so you can check off a box in your canned script before you allow me to even schedule a Genius Bar appointment. Where once again they will pretend to look for a fault with my keyboard because they’re not allowed to admit there’s an issue in iOS 11.

On the day I finally gave in to go exploring Android and Windows alternatives in person after a year and a half of repetitive, ease of use-dampening issues from iOS and my Apple devices, this bullshit keyboard support dance of death beginning all over again was the moment I finally gave up. I ended the chat, walked back to the Apple Store, asked for the manager on duty, and thanked them in advance for letting me verbally offload my year and a half of frustration over my over-again keyboard issues, and the context of Apple Support being unable (or unwilling) to truly resolve anything on the very day I spent finally playing with the devices I could turn to if I ever chose to walk away from iOS–and Apple.

I didn’t ask for anything. I didn’t want anything other than to be heard as an Apple user at the moment when, after many years of being an Apple user, I finally realized I didn’t have any faith left in Apple. At least not Apple under Tim Cook. There’s no excuse for devices and accessories and OSes all specifically engineered for each other to only intermittently work after almost two years on the market. There’s no reason to have to suffer through core mobile apps with outdated features because they’re all built around decade-old code. There’s no reason for the ease-of-use of Siri and Apple’s dictation engine to be literally years behind the competition from Google and Amazon.

And there’s no reason other than Apple trying to save money at the expense of customer times to put this year so many roadblocks in front of the more than decade-old practice of allowing Apple users to make Genius Bar appointments on their own. That’s not a brand-friendly Steve Jobs policy. That’s a bottom-line-is-all-that-matters Tim Cook policy. And like so many other Apple decisions made in this users-come-last Tim Cook era, it stinks.

And to be honest, I’m completely over it stinking, and for that stench to directly impact how well I am able to use–or even whether I am able to use at all–my Apple devices. And not for nothing but…

I’VE BEEN HERE BEFORE AND I’VE GOT THE BLOG SERIES TO PROVE IT. Eight years ago I began my first migration away from Apple for essentially the same reasons. Back then, after so many years as an exclusive Apple user, leaving was a very difficult, even emotional decision. Not this time. Six months from now I’ll be free to upgrade both my iPhone and my iPad Pro.

Or as I finally allowed myself tro admit yesterday, get rid off.

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