I don't have an answer to all your questions, but there will always be a fundamental conflict of interest between privacy & security (of the end user) and market forces. You can hope for more usable systems that are also secure. If you are put off by Tails or usb sticks and different devices, look at QubesOs. They also have a good approach to security, but even they are having a hard time finding hardware that meets their requirements. In the end, you, as an end-user, will have to pick your trade-offs.