The people who have decision making authority or political weight, doctors and administrators are completely clueless. While typically highly intelligent, their training tends to turn them into savants.
These people making decisions, and the users in nursing all ask their kids for help at home with this type of stuff. IT staff have to support a userbase that is much older than most other industries (http://www.vcstar.com/news/2010/jul/10/records-show-about-ha...). IT cannot assume competence.
There is absolutely no incentive to get this stuff right. Most healthcare systems are rolling in money, so IT staff levels are typically huge. The correct way to protect these fiefdoms is to not screw up and not get noticed. Admin will keep throwing money at you so long as they don't have to think about you.
In the health system, IT has no political weight. It's regarded slightly better than janitorial staff. Which affects (non-monetary) resource allocation and recruitment of IT talent.
A brief anecdote. The College of Pharmacy had a contest requiring some of the hospital's pharmacists to score videos of student-patient interviews. They had to do it at home. There are departments at the hospital that do incredible work and research with imaging tech, but their pharmacists can't view a 5 minute video clip in any format.
Honestly. When you have 12 managers for ONE project, that has ONE developer, nothing gets done!
Outsiders think the reason it's so hard is because of dealing with 'sensitive data' - they don't deal with it, they pretend they do.
If you want to make software for healthcare, have lots of cool graphs, lots of amazing "management" features and features to cut-down on paper-work (i.e. do referral forms automagically) you can sell it for A LOT -- but only if you're really good at sales, and know exactly the right people. :)
p.s. in healthcare IT, you can sell promises (oh, my humanity)
Another point would be the costs involved. Everyone seems to charge some insane multiple once it's healthcare-related, even though it's just the same hardware/software.
I guess there's a lot to talk about and discuss, drop me an email if you are interested. I'm also pretty sure the DrChrono guys (I've seen them post on HN before, I think) can chip in with a few insights from their end.
When designing systems for doctors, you really need to talk to them and watch them use your product/platform/software/website. There are a lot of idiosyncrasies/terminology involved which an outsider is unable to grasp easily.
I'm not saying this is why health care IT is so screwed up, but it's something that drove me away. There are standards for data storage, like HL7 and CDISC.
Now, add on the fact that you have to formally test the living crap out of anything healthcare related, or people can die. The bureaucracy can be a lot for some people to put up with. It's difficult to attract good developers, when there are so many other fields to work in that are more free-wheeling. Also, healthcare IT is not very conducive to a lean startup culture, because of the domain expertise and labor involved to get a product out the door.
I recently left my job at UC Irvine, where I worked in telemedicine research and IT. I can only repeat what ahi and veb have already said, bureaucracy, specifically bureaucracy on all levels, departments, organizations, insurance companies, state and federal bodied, regulations, and fear, are the cause for stagnation. I've seen too many innovative solutions squashed because someone in management was convinced it wasn't "HIPAA-compliant".
If I had to choose one reason, however, it would be insurance companies. Why? Insurance companies choose what to reimburse, and they're not reimbursing for technology-based preventative and/or virtual care. My first response on HN was on this exact subject: http://news.ycombinator.com/item?id=2256119
It would be so easy to require dr's to give a little information about how they cut costs and Anthem could deliver that information to consumers online.
Instead Anthem does nothing. Why is Anthem such a big player? They suck.
The data is stored digitally. For some reason or another her office only sends the data to the customer through snail mail.
I've heard on a few web sites that they still do it the harder way, as opposed to email, to get extra money from the healthcare companies.
The system, as it is today, does not encourage players to be efficient.
Most doc offices aren't tech savvy - they'll get something that has some approval from colleagues or professional bodies, and go with that recommendation. The few products/services that can break through that seem to be set for a while.