I have a chance to buy a used 2008 Trek 4500 for $375. Good shape and rides nice. Any thoughts on the price? Might offer $300.

i think $300 would be awesome, but $350 may be a legitimate price

Sold for around $500 plus or minus new. It is 2.5 years old now. $300 would be my top giving price if it is in like new condition. These things depreciate quickly but the value is dictated by the buyer however, and that is you in this instance. Good luck.