People will tolerate a reasonable level of technical difficulty if it's worth it. For example, what if you could only buy iPads with btc? It would incentivize the masses to find easiest ways to use them. A super simple solution would eventually evolve.

I don't think user experience is limiting bitcoin much. The lack of mainstream BTC-dependent services is what is limiting bitcoin. As soon as a tentpole application is developed, managing btc will quickly fade as an obstacle to adoption.