I agree to some degree (!) but I believe a lot of the software used by medical personnel in their daily routines could use an overhaul, plus numerous other modern tools could be given to them for daily use.
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.