Make a silly offer, and act like you don't know any better. Something like $500.
The worst that will happen, is the owner laughs, and you then act like you feel stupid for "not knowing any better". It's the easiest way to get stuff cheap. I do it all the time.
The other way is to act like you know something they don't know. Sometimes, you can give out that one little detail that tells people that your offer is "probably the best offer", and confidence will help show that.
The latter is my primary technique when it comes to cars and automobiles, like my new Tacoma.
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"¿ʞɐǝɹɟ ɐ ǝɹ,noʎ uǝɥʍ 'ʇı ʇ,usı 'ʎlǝuol s,ʇı"
