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Usually if I am making low end offer I will typically say something along the lines of, "I know this is wroth more, but this is what it is worth to me"....... figured what little I could pay was an insult; I found out later that they sold it to someone else for even less.
Another key is letting people know what you plan on doing with it. Some are interested in money and think you are just going to flip it and dont like that, other have sentimental value. If you plan on keeping it and using it, sharing that can help.
Other times I find something I am interested in and I will mostly follow the first approach. I will tell them I am interested, but my price is $$$ and is a standing offer if they do not sell and I tell them I hope they get their full value.
All 3 of these have worked well for me and usually keep the drama/possible hurt feelings out of it.