As you may have heard on this week’s episode of our podcast, You Chose Poorly (listen on Mixcloud here and subscribe on iTunes here!) I’m a proud owner of 12.9″ iPad Pro. A Hurry up the Cakes review is coming soon, but I think I have to sort out my many unprocessed feelings about it.

I know that I love it. I know that I love multitasking on the big-ass screen. I love using the Apple Pencil to make stuff on Paper and Procreate, and to mark up students’ papers on Microsoft Word. I love using the Smart Keyboard Cover and having the option to use my iPad as “just” an iPad, or as my work machine. Its size is perfect for writing, for drawing, for multi-tasking, for reading in landscape, and for catching on the WWE Network. I love it. I love it all.

As a device, in and of itself, it is, without question, the very best iPad that I have ever owned, and the one that I am or have been happiest about.

However, as you also may have heard on this week’s episode of You Chose Poorly (listen on Mixcloud here, subscribe on iTunes here!), I can’t help but see the iPad in the contexts all the other iPads that there have ever been, and all the other iPads that are on sale right now.

It’s in the these two contexts that I think I’m gaining some mild anxiety.

My “Wrong” iPads

The “New” iPad

Four years ago, I upgraded from an iPad 2 to the “New” (3rd generation) iPad. It was something I was immensely excited about. I scarfed down every review, every first-impressions article, every post that concerned itself with Apple’s then-latest-and-greatest.

Nobody warned me that I would regret it.

Sure, it was a little bit thicker and heavier than the iPad 2. Sure, its processor was only an “X” upgrade (A5X from the iPad 2’s A5). But it had a retina screen. My iPhone had a retina screen and it was always very jarring to shift between my phone and my iPad. Also, the new iPad was pretty.

Nobody warned me that I would regret it.

Nobody warned me that Apple would release a brand new iPad, with an A6X processor and a lightning port, just six months later.

Six months. It broke my heart.

Not only because the 3rd Generation iPad was no longer the top-of-the-line offering, but because it became more and more evident that the A5X chip, when pushing the pixels on a Retina screen, isn’t that much faster than the A5. In fact, it was actually slower, in some ways. It was the 4th generation iPad that ended up being the true One Generation Jump over the iPad 2. The iPad 3 was just a stopgap measure—besides the Retina display, it was more like a .5 generation jump.

So when Apple announced the iPad Air in one year later, I knew I had to upgrade to it.

iPad Air

Apple launched the iPad Air in October of 2013. I was beginning to be uncertain about whether or not one year was the right amount of time between iPad upgrades, but I was already antsy about getting a new one 18 months into my iPad’s life cycle.

So, then, the iPad Air. One pound. iPad mini-esque redesign. Accidental bezel touch non-recognition technology. Lightning port. A7 chip. Why wouldn’t I get it, right?

So I did. And I was very happy with it. (Also it was legitimately a very difficult time in my life, and Apple came through at the right moment to provide an opportunity for retail therapy.)

The next year, when the iPad Air 2 launched, I barely paid any attention. I was engaged to be married, and spending money on what seemed like a minor upgrade (laminated screen, Touch ID, 2GB RAM, A8X chip) wasn’t exactly a high priority. Also, my wife adds, I was “deliriously happy and nothing else mattered.” (She’s been reading over my shoulder, apparently.) I even used it to read my vows during my wedding!

For a while, everything in my iPad world was pretty darned good. Until iOS 9.

During the WWDC 2015 keynote, Craig Federighi announced and demoed iOS 9’s new features for the iPad: keyboard shortcuts, command-tab app switching, Slideover, and the big one: Split Screen Multitasking. I was pumped. My iPad Air’s life cycle suddenly got an unexpected boost.

And then they announced that only the iPad Air 2 would have all the new features. My iPad Air would get everything except the big one.

Suddenly it all began to make sense. The A8X chip was not just a One Generation Jump over the A7, but a full generation and a half. And it had 2GB of RAM—more memory than iOS truly needed just six months before. My iPad Air was a very good upgrade in 2013, but the iPad Air 2 was a way overpowered, future-proof fantastic upgrade in 2014. In 2015, the Air 2 hardware would begin to truly sing, while the Air 1 would start showing its wrinkles.

Once again, I had the wrong iPad.

(I mean, I loved it, but it was wrong.)

iPads Pro

I kept my iPad for a little while longer. In September, at the launch of the iPhone 6s and the new Apple TV, Apple squeezed in an announcement for the new 12.9″ iPad Pro, along with the Smart Keyboard Cover and Apple Pencil. In December, it arrived here in the Philippines, sans Pencil and Keyboard.

By March, nearly all local Apple resellers had demo units of the Apple Pencil. So I dropped by one store and tried it out. It ruined my day. (This story, and many others are told I full detail in this week’s episode of You Chose Poorly! Listen on Mixcloud here and subscribe on iTunes here!)

So now I’m a very happy owner of a 12.9“ iPad Pro. I’m pretty confident it’s the ”right” iPad for me simply because it’s what I wanted, and I love it, and I use it all the time, and it delights me.

That’s all that’s supposed to matter, right?

Except the new 9.7″ Pro seems like it’s the new star of the iPad show. And the True Tone sensor and the wider gamut display seem like the new hotness of the industry. And it’s thin and light and much more bringable. And my iPad doesn’t have them. And I think Rene Ritchie and John Gruber like it more than the big one.

If you pretend that I don’t have an iPad, and you make me choose between the baby Pro and the large Pro, I would still choose the larger Pro. And I would be happy. And the whole premise of this post wouldn’t even be an issue.

And then on Tuesday morning, I record another episode of You Chose Poorly (listen on Mixcloud here and subscribe on iTunes here!), and wonder all over again. I have the 12.9″ iPad Pro—I chose well, right?