Ultimately, I see the issue to be one of choice. I want to give people the ultimate ala carte experience. Whatever you have on hand, plug it in and I'll tell you the rest you need to get your small retail business running.
Some people don't want to buy an iPad. They already have a 4 year old laptop and that really should be good enough. Or they are ultraconservative and think the iPad is an iPassingFad. IDK, whatever people have for reasons to want choice, I don't really care. More choice is a good thing.
One of my hopes is that, by enumerating the ecosystem and smoothing over how the parts interact with each other, I can blaze a trail for others to follow and offer services for the individual parts. Competition drives prices down.
So that means, you can either run your own server or contract out to someone else. There will be people who care about hosting-their-own solution, and there will be people who don't care. And for the majority of them on either side, the current state of affairs is a murky cloud of poorly understood information.
How is it possible that there can be so many different POS offerings in the world? Each market has its own dominant system, and they are very often a locally developed system. You can't tell me that there are so many valid opinions on how to track inventory and sales that it warrants a different system per city. It's a lack of information that is the problem.
It's also fear. A lot of business owners are very willing to pay big bucks to be able to pass the buck. They can buy a POS system with a service contract and say "it's taken care of". My interviews have indicated that this is the vast majority of cases, that people tend to buy the system with the least amount of friction (and in many cases, "taking the time to learn about 2nd or 3rd options" is significant friction).
PG talks about how bad technology can continue to dominate a market because it's not an interesting enough problem for hackers to overturn. I think a lot of people don't see the POS software itself as that interest, and see the payment issue as too scary, that they aren't throwing their hat into the ring to build this sort of software.
Think about it, what bigger market of customers that you know are more than willing to pay big bucks for a system at the drop of a hat for bog-standard CRUD apps than small businesses in need of POS? Yet why are there so many "social photosharing" startups. There's almost no revenue proposition out of an Instagram-like (Instagram may have a revenue proposition, but being an Instagram knock-off isn't going to get you the same sauce). Yet that's where everyone is at: writing their own JavaScript templating engine to serve up social photosharing.
And I just think it's because social photosharing is very well understood. POS is not because of the auditing and payment issue. And it's not glamorous, though I think it could be if it weren't so scary. So, I'd like to ask Mr. Gorbachev to tear down this wall.