Within that goal, we're looking at various pricing options, and additional bundled or a la carte services (DLP, logging, backup, etc.). $99/mo is just intended to communicate that if you want a single user VPN to use BitTorrent or IRC, you should look elsewhere. (I'll probably put up some Tor nodes again on separate networks to contribute to the "freedom of information" market)
The CloudFlare analogy is kind of a stretch, but the idea is that they do magic stuff to your front end customer traffic, and we do magic stuff to your back end internal user traffic. They're performance and security (mainly availability, some other security); we're manageability and security.
As for why you'd use a service vs. setting up a server and running it yourself, different users have different internal support costs for different things. I run my own services for some things. I use providers for others. Most businesses are generally happier buying a packaged service vs. paying someone to configure something custom and put it on a server and maintain it. It really depends on the environment.
I also don't get the comparison to CloudFlare. CF is a proxy service that optimizes and protects your site from attacks. A VPN provides a secure connection between computers. The only thing that's the same is that they're both security related.
Edit: After re-reading the article, looking at the site, and comments I realized I've misunderstood the service. The TC article made it sound like you were just selling VPN software. Now I understand that you're acting as an intermediary server, allowing clients to connect without setting up their own. It's an interesting idea but my first question still stands. Why not pay someone to setup a server for you?