Really, an order of magnitude more? Entry-level Mac Pro, quad core 3.2 Ghz Zeon, 6 GB of RAM, 1 TB HD, and ATI Radeon HD 5770 costs $2,500. I'd love to buy that at the $250 price-point. Please share.
Over priced? Yes, but numbers have meaning.
This. Except don't use Google Docs. I can't imagine using Google Docs to store 20+ years worth of documents. Google Docs is good for collaborating to create/modify a document, then allow you to take that out when you are done, and organize it how you want. Create a file server (probably what you currently have), and put things into folders in a sensible way. By year, by topic, by whatever will make it easier to sort through. I'm sure Bob realizes the mess that has been created. Just say "This has become disorganized over the years, let's make a conscious effort to organize it." It's not Bob's fault, it's everyone who didn't say something sooner that is to blame.
I read it as "It is price x no matter what, while a DDoS is in progress, the price increases to y, even if you bought it ahead of time" which would be gouging. If it is, indeed, "Price x if you buy it ahead of time, and price y if you buy it during an attack" then that's just common sense. Ongoing protection that might not be needed is going to be cheaper than ongoing protection that is needed immediately.
That said, it sounds like the guy had warning before the attack started, so this is more like buying homeowner's insurance after someone threatens to burn down your house.
Nobody said computers were going to be polite.