Guess I'm an outlier here, but I usually ask (and, this goes for cars, bikes, any kind of stuff of any significant value) questions like, "how much do you have in it" (which offers a chance to mix up purchase price + parts/upgrades), "why are you selling it?" and "how long have you had it?" To me, those all seem relevant and if a seller gets uncomfortable answering any of them it seems a little sketchy to me. I mean, there are very legitimate answers (of which I have all provided, honestly, when asked) like, "I bought it for $50, put a couple hundred bucks in parts on it, owned it for 5 years and now the market puts the value of a ____ like this at about $500 so that's what I'm asking", "I'm selling it because I really only bought it as part of a package deal with some other bikes and I'm trying to recoup part of the money I spent" or "It's a great bike, but it's a little too big for me", and "I've only owned it a short amount of time...wasn't sure what I'd do with it, but had an opportunity to purchase it and did since I knew that it's a desirable model and I'd have no trouble selling it".

There are a lot of factors in negotiating a deal on something like a bike and some people (me included, I suppose) enjoy the sort of creative aspect of navigating through working out a deal. The thing is that the price is *not* the only factor in the deal. Sometimes it's timing, sometimes it's the seller knowing the bike/car/etc. is going to someone who appreciates it the way they do, or whatever. I've also quite comfortably bought bikes and cars from people who are flipping them. I usually ask people what they paid for things (even if they aren't selling them) mostly out of interest in keeping a sort of 'intuitive' feel for the market of things I may be interested in buying at some point. There have been times when I've inquired on a friends' bike/car/etc. and the conversation ended with me offering them a price with a nice bit of profit built in where they get a quick flip and I get whatever it is that I was looking for...in other words, just because I ask someone questions like that does NOT mean or imply that I expect them to take a loss, not make a profit, etc. Of course, when I see the stuff listed for 10% of the market price on the local craigslist, I don't usually go and offer more than the asking price.....

anyway, another perspective & I suppose the conglomeration of the whole lot of them is what makes the world interesting.