Why hasn't the POS problem been solved yet? I'm assuming there's either some blindingly complex/simple reason because it's a large problem that frustrates a lot of people.
In my (limited and anecdotal) experience, many people who have the purchasing power for these systems just go with something that their payment processor recommends (or sells themselves). They see it as a cost rather than as an opportunity for efficiency (read: more money).
There's also this kind of "blood sweat and tears" attitude with a lot of food service management, and so things they see as conveniences are a sign of weakness.
There's also the fact that switching POS/ordering systems requires re-entering the entire menu and all options, and it's often management who's expected to do that.
All of these things (again, in my observations) add up to a much smaller actual market for selling such devices than one might think at first blush.
I've viewed it in the same light as all other enterprise software development & purchases--neither the developers nor purchasers of POS software are going to be using it, so bad things are built and bought, with some exceptions. It just takes a long time for the tide to change in the industry.
There are good solutions out there. I'm currently working for a startup that's doing iPad based POS.
Without trying to toot our horn, it's a lot better than any of the legacy systems out there.
So no, there ins't really a reason why there isn't a solution except that nobody has made one yet (except for us and a couple of other tablet based POS systems).
I don't know if this is kosher or not on HN (still relatively new to posting here), but what is your startup? I think that would be a space I am interested in and would love to learn more.
This is my experience, having worked in POS systems for a few years. The customers - especially huge ones like Walmart, Target, USPS - buy these systems on the order of once every 10-20 years for any given store. They don't want to upgrade them because they're expensive. Also, the companies that make the traditional ones were not very innovative when I worked there (20 years ago). Windows 98 had shipped and they were still using DOS on new systems.