My overall point with that sentence was that the more tech literate someone is, the less likely they are to benefit from the ease-of-use gains, and the more tech literate someone is, the more likely they are to regularly utilize their "lost freedoms". I phrased it poorly, my apologies.
Abstracting away the hierarchical file system is a positive for my mom, who can never find stuff she's saved, but I have no issues using one in the first place, so my gains are smaller. She'll be thrilled not to have to navigate an application installer or download some component from the web to run something, but doing that is nearly effortless for me.
It's no loss at all to my Mom that the iPad can't run some GPL Ruby VOIP app she wrote herself, because she can't write a Ruby VOIP app. By contrast, I would be giving up my ability to write and run my own Ruby VOIP app[1].
Overall, I (as a very tech literate person) benefit less from the positives and feel the pinch of the negatives more than my mom (or any less tech literate person). It could still be a good trade for me, but I wind up looking at a totally different values proposition than my mother would.
[1] - I have no interest in writing a VOIP app.