"... the equation for me was surprisingly tilted in favor of Android thanks to the simplicity of developing for it. Having gone through the process, I have a clearer understanding of Google’s strategy: I think they hope to win because their platform is so much more developer friendly"

On the open-source front, the only option I know is ownCloud. It provides the software to build your 'Cloud' storage, but you must provide your own hardware.

On the other side, you can try Wuala. It is not Open Source, but it encrypts all your files before uploading them. There are clients for almost every platform.

"A paperless office is as useful as a paperless toilet. Some things would be impractical..."

Let me introduce you to The Bidet

"Why does every single computer need to be geek friendly?"

Because a potential geek can be born in any family, and unless you are planning to offshore all your engineer task to China, you will need these people. I have a M.Sc. in Computer Science thanks of the interest in programming I grew by tinkering with a C64 when I was a child.