Posted by on June 6, 2012

Before I bought an iPad, able to finally justify it because I had a client who wanted me to write software for it, I didn’t really understand the need for one. I’ve been using a laptop as my only computer for at least 14 years or so, and with the iPhone to provide even more portable computing, I felt like the iPad didn’t really offer anything that I didn’t already have. For major computing tasks I had my laptop, and the iPhone was seemed perfect for reading books in iBooks or websites with Instapaper.

When I first bought the iPad, it was solely for work. The only app I installed was FileMaker Go so that I could test the software I was writing. Soon, of course, I began to look at other apps, first iBooks and Instpaper, but eventually games and other productivity software such as OmniFocus. Now my iPhone has been relegated to a, well, phone (ok, and camera for stills and video, and audio player for music and podcasts). Nearly all my reading is now done on the iPad, whether its a web site in Safari, a book in iBooks or an article in Instapaper.

In fact, I’m reading more now than ever before, and most of the reading is done with iBooks on the iPad. I use it to reference design documents in PDF that I’ve written for clients, read classics downloaded from Project Gutenberg, But one unfortunate side effect of using iBooks ever more and more is coming to terms with the limitaitons of managing books using iBooks and iTunes.

First of all, I already have hundreds of books in iTunes. An exact count (with a smart playlist that includes anything where the Kind is either “Book” or contains “PDF”) is 520. Some of those are software manuals in PDF form, some are free novels available from writers such as Cory Doctorow, but most are public domain works such as the either from the iTunes store or Project Gutenberg. I’ve probably spent less than $10 on books from iTunes. It’s really amazing how much free works there are available.

But with all those books, it’s very difficult to manage them in iTunes.

Here’s what I would expect is possible in iTunes: complete and easy management of books and synchronization of bookmarks, notes and last left reading locations across devices. Some of this does happen, especially synchronization. I can read a book on the iPad, sync that device, then sync my iPhone, and if I happen to have the same book on the phone, can pick up (almost) exactly where I left off. (“Almost” because it appears that one device picks up where the screen began the book on the other, and since the iPad can show more of a book, the iPhone usually restores my reading just before I had left off.)

Even the syncing isn’t all it should be. I shouldn’t have to syncrhonize both devices (in the right order) for everything to get from one device to another. Why isn’t [iCloud][] taking care of that? (For that matter, why do I have to manually sync at all? Why can’t the device simply perform a periodic sync without me having to do anything?) And although where I left off is synced, the bookmarks and notes aren’t (at least as far as I can tell with my quick testing).

But the real trouble is getting the books I want to read, and only the books I want to read, from my computer to the devices. iTunes reveals a host of useful ways to organize its contents. With smart playlists and tags such as Grouping or Comments, it’s very easy to create playlists that include exactly what I want.

I do this all the time with music. My daughter (like her father) is a huge Weird Al fan, and I have all of his albums in iTunes. Being famous for his parodies, I also happen to have most of the songs he parodied. We often like to listen to one of his parodies and then marvel at how well crafted it is by then listening to the original. So, for each of his parodies and each of the songs I have that was parodied, I set the Grouping to “Weird Al Parody”. Not a smart playlist can bring all of those into one place so we can easily enjoy the music.

wierd al playlist

Creating a smart playlist of books is very easy also. The problem is, I can’t do anything useful with it! Let’s say that I’m interested in having 20 or so books on my iPad and iPhone. I can easily find them in my library and set the grouping of each one of them to “Read Soon” and then create a smart playlist that includes those 20 books. But if I then go to the Books tab while the device is selected, there’s absolutely no way to say to iTunes, “Put my ‘Read Soon’ playlist on the iPad.” Instead, even though I have that playlist, I have to navigate an insanely small window that shows only 15 books at a time and select each book individually. And that tiny window is horid to scroll through. Sometimes, for reasons I’ve not yet figured out, it will just scroll to the top after I’ve finally gotten to the T’s to find A Tale of Two Cities, forcing me to scroll all the way back down again.

books tab

Collections themselves in iBooks are problematic. ePub books, by default, go in the Books collection while PDFs go into the PDFs collection. Really, what do I care which format it is? I’ve actually created an “All” collection and whenever I sync a book for the first time and find it in Books or PDFs, I move it to All. From there it’ll stay for a while until I move it to my “Current” collection, which is, rather obviously, the books I’m currently reading. Finally, collections are mutually exclusive. A book can only be in one collection at a time, unlike songs in playlists. On the other hand, I can sync two music playlists to my iPhone and each of them can have many of the same songs as the other.

Really, all of this could be easily solved by treating the syncing of books more like music. Apple’s done an extraordinary job of making it wonderfully easy to get exactly the music I want, or even the random music it chooses for me, from my Mac to both the iPhone and iPad by using smart playlists. Just allowing me to use the same feature for syncing books (and, for that matter, allowing playlists to conform to collections and folders of collections) would solve 90% of my troubles with iBooks. Honestly, I barely use the notes and bookmarks (although I hope to more as I go further into my study of the classics). If they sycned notes and bookmarks, that would just be icing for me.

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