True unless someone has made years of investments in iTunes-sourced content, then moving over to a cheaper phone with the same feature set is no longer an apples-to-apples comparison. I have a collection that goes back to iTunes' and the iPod's very first days. I'm not terribly keen going through any conversion/repurchasing process.
If you bought your music after Apple finally ditched DRM, you can upload your AAC files to Google Music for free and sync/stream them to all your Android devices as well as your laptops/desktops.
If you "bought" your music with Apple DRM, you can pay another fee to actually own it and be able to play it on a non-Apple devices.
If you "bought" your videos with Apple DRM, consider it a lesson learned.
Taking the entire migration process you describe changes the "price" to be paid for similar phone, so my claim of false equivalence still stands.
There's no "lesson" when I have made the conscious decision to stick with Apple all these years. I may have paid a premium paying for iPods and iPhones, but I feel my time is valuable enough to not have to mess around with my media files in any way you describe. Nor do I feel the urge to spend money on music I have already purchased, but I don't see that as being a mistake from which to learn a lesson. Nothing has happened to me with Apple or its products so egregious to feel compelled to take on anything like you describe.
The 'mess around' process would just mean loading your existing music into Google Music one time. Heck, on a Mac, it may just ask by default if you want to sync your iTunes library. Then they're available everywhere you run Google Music... which means not being artificially locked to a single company's hardware.
Most people make the mistake to think they 'bought' a movie or DRMed music file when they really just rent/lease it long term.. And then they realize they're screwed when they want to the freedom to buy whatever device they want and have 'their' music they 'bought' on it. After all, most people didn't grow up buying a CD from Best Buy and having it work on their Best Buy CD player but not on their Sony CD player.
You may have realized what you bought into and consciously made the decision that you accepted the limitation in rights/etc in exchange for convenience/etc, but most average consumers do not.
Remember that music on on iTunes isn't DRMed anymore.
With movies you're SOL, but Google Play literally let me just upload my iTunes music folder, and aside from a couple of metadata glitches, it just worked.
