Some of these guys don't want to pay sh/t for stuff and that's fine. The way I look at it, I don't want to spend ten years looking for the perfect deal so I can save $50.

Must admit that I personally tend to be a tight arsed git on most occasions, (it's the way we're brought up around here. If you can't nip a currant into quarters and make a meal from it, you ain't worthy of being called a Yorkshireman

), but there are occasions where it's prudent to pay more. Restoration projects, for example, will take time hence cheap is always good. You know it's not going to be pressed into use immediately, so time isn't of the essence. However, if it's a machine needed straight away for putting to work, best to spend that bit more and get one as soon as and which doesn't need work to get it usable. It's swings and roundabouts.
Plus, as mentioned earlier, the location really can make a lot of difference. There are certain areas, not a massive distance away from me, where I love to see stuff listed on Ebay, for example, as I know full well the final price is likely to be lower there. It's as if people just don't want to venture there, for some reason.

Look down South though, and the expectation of what something is worth can tend to be silly from the onset.
End of the day, any item is only worth what someone is willing to spend, whether that be as little as possible or whether they're willing to literally throw money at something. Peoples idea of what classes as expensive vary. A wealthy person, for example, could drop an amount on something as if it's nothing, whereas for another person that could be a year or more of wages. Perspective and means are large factors in any sale.