I have long been a self proclaimed treasure hunter. I love to get a good deal, as do many of you guys on here. I have often found that it can create a difficult situation when an item is priced higher than what we are comfortable spending or we think there is an opportunity to get a better deal. Any ad with O.B.O is a perfect example.
I have taken the following approach based on advice from a cousin of mine who has been a collector and dealer of antiques for decades.
When I find something I like, I decide whether I will buy it at the price listed. If not, then I am totally prepared to walk away and often do. We have all been to sales, shops, etc in which the prices are just unreasonably high.
If I will buy it at the offered price anyway, then I ask the following question. " Are you flexible on the price?" This is non-threatening and it doesn't put you in a position of offering a price too low and insulting the person. They will say yes or no. If they say no, I buy the item at the offered price. If they are flexible, then I just saved some bucks.
I find this approach very easy and it isn't as uncomfortable for buyer or seller. FWIW.
I ask if they are flexible on the price whether I would pay the askining amount or not, unless they say price is "firm" with lots of exclamation points.
Yes, I do sometimes as well, and I think its a better approach than trying to figure out how much the seller will lower price and trying to offer a price at them. When you say "Will you take xxx" You have just told them that their item isn't worth what they think it is. It can cause more defensiveness and can result in them just saying no.