I like to haggle unless it's already at a price so low that it would be insulting to ask lower. It's just a habit I picked up from my parents.
I do a lot of buying of accessories, strings, picks, cases, etc. I'd like to think that an extra $30-$100 saved could go into something incredibly useful and I'd be foolish not to at least try to haggle it down. I always give it a shot at my local music stores and usually we come to a nice middle ground. Same with craigslist sellers.
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