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I have a 9 year old son and we are looking at a small adult bike and he is a small 9 year old. I second talking to the guys at Great Escape. They helped us a lot when we bought his last bike (his learning bike) and gave us lots of great ideas on how to teach him quickly. Once you go to some of the local shops if you feel that is too much to pay you may want to check out REI. They would be my next choice after a bike specialty shop.
Learning how to maintain and fix small problems on a bicycle is a great way to teach valuable skills to a youngster. Even if you are a klutz with tools with the help of your kid you can probably figure it out. Don't spend $500 on a bike to learn on. A $20 garage sale special can be a great machine to learn on. Let your kid "customize" it the way he sees fit. Learning how to barter and trade for the parts he needs with other kids is another learning experience.
I was in the same situation as you about a year ago (needed a quality bike for my young daughter) - unfortunately, most local bike shops in the Upstate do not sell used bikes - you might be able to get an "end of the model year" discount on a new bike. My preferred LBS is Great Escape - the customer service is outstanding.
I browsed Craigslist for months until someone happened to be selling a gently used Gary Fisher kids bike - it was perfect and the price was fantastic (only $80) - though I did have to drive to Spartanburg to get it.
There is a man that lives across from the YMCA in Easley. He has sold second hand bikes for years and usually has a large selection. You might want to check him out.
I always see various sorts of bicycles for sale when I go to Goodwill stores. Some are in bettter shape than others, but it might be worth a shot if you have the time.
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