Well, for starters, if money is no object then everybody is free. It kind of defeats the whole point of the argument to take such an important constraint away and then pose the question "how am I constrained?". Keep in mind that Apple's whole ecosystem is closed, not just their devices. I can't read their iBooks on my Android tablet, play their games on anything but Apple hardware, etc. Even the connector is patented to control every single digital bit that travels to and from the device. So in 10 years from now you might be up for much more than "hundreds" but thousands or tens of thousands if you have accumulated your lifetime library of content there.

But more seriously, your solution works only as long as there is "something else". So you're predicating the whole thing on the fact that there's an external entity out there for you to flee to. The problem is that we're moving headlong into a dystopian future where there simply isn't any ecosystem left where you can go. The least worst option at the moment is Android because it allows side loading and is open source so if Google turns evil enough you can be sure that someone else will come in and fork it to compete with them (you can argue that already happened). You can even create your own builds and deploy them to your phone if necessary. Now I'm not advocating any such extreme tin-foil type things in reality, but I do think it's vitally important we preserve at least the ability or freedom for these options to occur, because they keep all the other players honest.