The server side is pretty well set. The server code is open source, so feel free to setup your own server. If you use icecondor.com, the easiest option, then tracking history is free for the most recent X hours. By paying $Y a month, the history is tracked for as long as the account is current.
The client side is more complicated. The first idea was a free client, especially since the market was free-apps-only. Its the classic balance of income vs. adoption. I've since gone back to idea of putting the app on the market for $Z dollars. Z probably equals 2. The 1,000 downloads a week of WhatIsMyIp? is encouraging.
The open-source bomb, which Dietrich reminded me of last night, and I am glad exists because thats the point of open source, is someone could download the icecondor source, build the app, then post it in the market as a free app. Or even a paid app at a lesser cost. Its something I hope does not happen but if it does, then the website services will become its only profit model, just like in the original plan.
The biggest question mark right now is, is it possible to do a trial version? My guess is the market will not explicitly support a trial version. What seems to be a popular route is to publish a free, limited app, and a second paid app with full functionality.