Secure messaging was the same for a long time but now it's improving rapidly. I don't think managing keys will get harder and harder. Already using a Ledger Nano is pretty nice, and I imagine in a couple of years it will be very nice. But I also imagine the ecosystem for hosted keys will stay, so you can choose to be your own bank or to trust some other actor. With cryptocurrency it will be much easier and cheaper to move to a competing service, too.