Normally, when I get an electronic device, I use it and wear it down until it’s nearly unworkable. Probably not very “high tech” of me, but that’s how I do it (I only recently replaced my 14+ year old Kindle, for example).

For once, though, I decided to upgrade my iPad setup before I ran my existing one into the ground. Mine was decent, maybe 6 or 7 years old (and I got it refurbished), and was a 2018 iPad Pro. I began the trade-in process when I started getting flashbacks from my previous iPad before that, where I wore it down so much that it barely charged, it had a $0 trade-in value, and Apple wouldn’t help me service it because it was so old and no longer supported… so I decided to be a bit more proactive this time.

I admit I’m not a hardcore tablet user, but I do juuuust enough that I wanted something with decent horsepower. On my iPad, typically, I:

Draw (with the Apple Pencil and Procreate)
Edit videos (with LumaFusion)
Write (with Obsidian, but not as much as I would like because I haven’t had a keyboard setup I liked)
Play games (Not wildly graphic-intensive ones, but like Clash of Clans, Civilization VI, and my daughter likes Lingokids)
Edit photos (mostly with Affinity Photo)
Watch shows (on various streaming platforms)
Read sheet music
Use it as a teleprompter

So anyway, not like… wildly ridiculous usage, but juuuust enough that I liked the idea of getting a Pro again.

My plan was to get the 11” one again, and potentially nab a keyboard case too. An 11” iPad Pro (M4) if you wanna look it up.

I… learned a lot during this upgrade process, both in good and frustrating ways, and I wanted to pass along my learnings here since I fell down so many YouTube rabbit holes trying to solve my exact wants.

If you have any knowledge of the Apple trade-in process, or even the common sense that “Apple is Apple” and that they change things a lot to make money… your reaction to this post might be, “well duh, Cassidy,” but I’m WRITING IT ANYWAY.

The size

They changed the proportions of the 11” tablet juuust a bit, and the back camera size changed, so I couldn’t use my previous case. I was not fully disappointed with that because I was considering a keyboard case anyway, but I was still surprised to see it.

The Apple Pencil

I was planning on just keeping my previous Apple Pencil, but when I got home after the tablet swap, I noticed that the magnet just wasn’t… sticking like it used to. The Pencil was flailing around a single magnet and falling off way too easily.

I thought it might be because of the lack of case, and then learned later (via a somewhat random video) that my 2nd generation Apple Pencil was not compatible with this new iPad. That was VERY annoying to learn, because the salesperson didn’t tell me that in the store! Oh well. I got a better deal on one with a 3rd party seller, heh.

A keyboard case

At first, I got the Apple Magic Keyboard case, and… nearly instantly returned it. Don’t get me wrong, it was a nice keyboard case, but it didn’t protect the sides of the device much, and it felt like it was turning my iPad into a laptop with almost no flexibility. I couldn’t remove the keyboard part from the case, and I couldn’t flip it around or anything to “just be a tablet” if that makes sense. It was rigid, and on top of that, wildly expensive.

Anyway, from there I did far too much research about cases, and the one thing that was still annoying to me was the fact that no keyboard cases on the market had a covered Apple Pencil holder. Like no pockets or sleeves or anything. I guess it kind of makes sense, in that a keyboard user is probably not drawing at the same time, but… I am that person that wants both.

It was quite frustrating searching for this, because I want to be able to toss my iPad in a backpack without worrying about the Pencil detaching. But, if I wanted a dedicated slot for it, I had to do a non-keyboard case. I literally just saw people using rubber bands and 3D printed brackets with their cases all over Reddit.

What I ended up getting (and we’ll see in a few months how I feel) is the Logitech Combo Touch keyboard case (refurbished, because it was still a bit too pricey for my taste), and a separate Apple Pencil holder to stick on the outside from the brand ESR.

I picked the Logitech keyboard case because the keyboard is detachable, and it had good coverage on the sides of the tablet. I have a toddler at home so I tried to look at robust-ness outside of just the case’s function, and it seemed to be the best of both worlds. I like that I can still have “just” a tablet, that it has multiple viewing angles with its stand, and that I can use the keyboard, too.

Miscellaneous things

Overall, not too many wild surprises, and a lot of this I could have known earlier if I did more pre-research, but… here we are. Here’s some final things I learned that are worth noting:

The camera moved on this iPad version, so it’s more landscape-mode friendly rather than portrait-mode. Not a big deal, but lightly affects FaceTime with iPhones.
If you don’t have iCloud storage, you can temporarily work around that when transferring iPads by doing a “backup to transfer” and get your current iPad backed up for around 2 weeks. If you want to do the transfer at an Apple Store, have your backup ready in advance.
You can’t trade in an Apple Pencil.
The final trade-in value of my older iPad was $214. Interestingly, a couple months ago it was at $230, so my own hemming and hawing cost me a bit, there. I don’t know how often Apple reduces the value of a device, but if you’re considering a trade-in, think about that!
You can’t trade something in for a refurbished item. I originally tried doing that by like “trading in” my older tablet for an Apple gift card and then using it on a refurbished one online, but something stopped that from happening and I didn’t bother to remember what that was.

I hope this is helpful to someone out there!