I do a decent amount of cycling and have a Garmin 305 that tracks heart rate, cadence (pedaling speed), location, and time. I always thought it would be a lot of fun to play with the data, and have been working on a site for a while with a couple friends that has some cool features (mouse over your elevation and see where it is on the map, determine time spent in heart rate zones, estimate power output in watts, calories, put it on a calendar - currently working on finding other times you rode the same section of road and race yourself)

Without a GPS unit, you can draw a route and we pull elevation data off our server if we have it (we have the continental US in 1/3 arc second accuracy, pretty good), estimate instantaneous grade, etc... fun project and people are finding it useful

Anyway, check it out if you want: ridewithgps.com

Do you use a piece of software for this? I've been slowly working on this http://github.com/zackham/time-tracula/tree/master to accomplish the exact type of tracking you describe.

Yes, it has changed a lot in the past few years, but it has only been around for four years and took time to mature. Deploying it has not been that difficult for a while now in a dedicated environment, and with Passenger (mod_rails) it is ridiculously simple even in a shared environment. Running Rails apps via CGI has not made sense for quite a while, even if you were using Fast CGI, Mongrel and a load balancing proxy have performed better and been easier to set up for quite some time.

Also, I'm not sure exactly what you mean about no debugging. ruby-debug works well, you can catch exceptions and do what you want with them, there are plenty of monitoring options, etc.