I'm late to this thread, but I'll toss in some examples of situations I've been in.
I put in stink bids all the time on eBay. I probably only get about 5% of the things for which I put in a bid. The main reason I do this, is that is that I really don't mind getting rejected. There is always another one that comes along and it doesn't take much effort.
I find that iPhone accessories are the best for this. I usually pay about $0.05 for three screen protectors, $0.25 for silicone skins, and $0.99 for charging cables. And this is the price including shipping, since for these types of things I only look for items with free shipping. The sellers for most of these are not recovering postage, let alone the eBay fees or price of the product.
Are sellers annoyed with me? Probably. But I benefit them. Keep in mind that I drove up the price for 25% of the items where I was the second highest bidder. I am the 2nd highest bidder much more often than I am the highest bidder.
Yeah, this is a different scenario than the one posted here, since it is an eBay auction. My willingness to do a stink bid and the amount of discount I look for is very much related to the amount of effort it takes to do so. On eBay, it only takes seconds. On something that takes an email, it might take a minute or two. I'm not as ridiculous for something where I know it will be rejected.
If someone posts something that I am interested in, I'll do different things. I've offered what they are asking if it is a good price and want to jump on it. I've offered a moderate discount (10-25%) if I think I can get it. Sometimes I have done this and settled on the asking price. I've offered 20-25% discounts on items where the price was great to begin with and had it accepted. I've personally never offered 50% for something that requires an email. The effort to success ratio isn't good enough for me. And I've seen many things where a fair price would be 50%, and just moved on because I figure the seller has no clue what a fair price would be. (e.g. I recently someone try to sell a used Kitchenaid mixer for more than it costs new. His listing even said that his price was firm)
On the flip side, when selling I've seen people disappointed in my not willing to budge on a price and lose out because they spent too much time bartering. This happened with selling Flames tickets here on CP. I sold some tickets near the end of the season for face value. A number of people tried to get a discount. I sold them at face value to the first people that offered it. Some of the people that offered a discount came back wanting to pay face value, but they were already sold.
The best barterer are those that know a fair price and know how easy it is to get it somewhere else. Most people are no where near that point, which is why you get ridiculous offers or people accepting sometihing that best for them.
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