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I don't need to be entertained, but I think most people probably do. I don't listen to music all the time, I like quiet, and the idea of being on the bike, and just 'being' wherever I am is much more appealing that listening to something and pretending I'm elsewhere. If I was doing that, why would I want to do TD at all!
As for tracking, no, nothing to do with phones, as there's only about 5-10% of the route with mobile coverage. It's by SPOT tracker (a gps transmitter) http://www.findmespot.eu/en/
turnpedal
hippy
Wow good luck mate, that's some serious riding. I remember doing the DD for the first time I didn't struggle with the physical aspect, my legs just switched to Auto after 50 miles, but I found it difficult to deal with being on a bike for so long. I mean that's only 120+50ish to Ipswich, and I don't do long rides all the time, nothing compared to this though. Have you thought about ways to keep yourself entertained? Or are you just going to use stray bears as motivation?
Also you mentioned the live-tracking, is that through a garmin/phone combo? I'm sure it's somewhere in this thread but I am lazy :)