I'm at the stage of the hobby where I have everything I "need". so nearly anything I see that interests me is not a "must have". therefore I generally don't get interested unless it is a "good deal".
That said, I like to make an offer. sometimes the seller takes it, sometimes not. I don't bother trying an offer if it is real overpriced, or my interest price is way lower than asking. When selling, I always have a bottom line price in the back of my mind, but I don't price high on purpose.
The most interesting deal I ever made was the seller making me an offer. I had walked by what I thought was a PRR caboose painted robins egg blue and lettered wabash listed for $90 (brass). It was a very nice job, but an awful color for PRR caboose - better on a 54 chevy convertible. I came back later in the day when things were quiet. the seller was there and we got to chatting so asked him if it was indeed a PRR ND caboose. he said yes and smiled sheepishly and made a comment about the color - I can't remember whether he got it that way or what. we chatted a little more and I started to walk away, and in my mind I thought I would maybe pay 50 for that but not anymore requiring repaint quickly! I never made an offer because I didn't need it and didn't want to insult him. Anyway, I got a few steps away and he said - "Would you buy it for $50?" I burst out laughing since I was thinking that, and I accepted his offer.
