It doesn't get much easier than "yum install" or "apt-get install".
Sure "apt-get install" installs the software, but configuring it to do anything useful is still anything but trivial. Installing Linux, creating a user accounts, setting up an SMTP, POP & IMAP server, installing a webmail app with spam filtering, making sure they all talk to each other, is hard. Installing WordPress is the easiest I've seen, and you still need to create a DB and copy the connection details.
I'm thinking of something as simple as you see a list of Apps (WordPress, PHPBB, etc). Just click 'install' and pick the directory you want it installed in. And you pay $.99 for the convince.
I think it would be good for the industry to move away from ad supported services, and to let users pay to host the services themselves.
I somewhat agree with your perspective, but think its going to be a hard sell. People buy apps because you don't have to think about it. Configuring a service is in direct opposition of that convenience, and I don't think you'll ever have enough training wheels in the interface to fix that.
I could be wrong.
Web Apps have been very good to developers. Zero piracy, no installation issues, low support costs. Users like them because it's simple to get started, they aren't tied to one computer. The downsides are all long term -- and it's hard to get people to think about the future, or things like privacy.
I'm not sure where the drive would come from to make it happen. I don't see which company would put in the investment to get it started.
It's got a long way to go before everyone can use it, but I'm finding more and more uses for it.