I am no expert on chain cleaning (yet), but I've done a fair amount of reading on it and can tell you tell you that there are SO many opinions on the best way of doing it, the best materials to use, how often to do it, whether to do it on the bike or off, etc. There are several thread on TE about it, lots more on www.roadbikereview.com, and an article on www.sheldonbrown.com (Here's the exact link: http://sheldonbrown.com/chains.html#cleaning). There is lots of conflicting advice out there and if you ask 10 people, you're likely to get 10 opinions.
As to whether it's time to clean your chain, that's hard to say. It depends largely on how many miles you have on the bike, the conditions you ride in, whether you regularly wipe your chain down and relube, and what kind of lube you use (dry, wet, wax, etc.). I cleaned mine recently at the 1,000 mark, and even though I wipe it down pretty thoroughly every 100 miles, it was pretty darn dirty.
When I cleaned my chain, I left it on the bike (I have a Campy ultranarrow chain and don't want to invest the money needed to buy the right chain tool to break it, buy a new masterlink, etc.). I sprayed it with an orange degreaser then scrubbed it with a toothbrush and soapy water until it "seemed" clean, rinsed it with fresh water and then dried it before relubing. I also cleaned the cassette, pulleys and chainrings the same way.
The toothbrush alone probably doesn't get it entirely clean and he degreaser will wear the chain down if not properly rinsed. I'm not too worried about it though. I think I'll stick with the toothbrush for now but make sure to rinse the chain a little better next time and will leave it out in the open air for a while to dry it before relubing. I am also interested in trying Prolink lube. Apparently, this "cleans" your chain while lubing it as well. Many swear by it.



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Seems to get the crud out a little better.
that I am pretty close to knowing more about my 3 month old bike. For the cost of the up keep, I could buy another bike.
I do spray and wipe down about every hundred miles.
