HIPAA (among other things) makes it Not Fun™ to be in that space. It's not that it isn't ripe—almost overripe—for an overhaul, but that the bureaucratic requirements tend to attract, well, bureaucratic types and reject people of a more "disruptive" nature. There's no particular reason why software and systems that can pass audits can't be as pleasant to use as any; it's just a matter of assembling a team of people that is creative, has both an aesthetic and ergonomic sensibility, and doesn't mind the kind of working environment that the process (and the auditors' interpretation of regulations; it doesn't matter what's actually required if nobody will certify that you've met the requirements) demands.