You know what, I'm going to have to respectfully take the devil's advocate on this discussion. I am a very frugal individual. I err on the side of being cheap more than I care to admit. My wife will attest to this. She constantly has to remind me that my cheap endeavors sometimes end up costing more more in the long run -- especially in my time spent.
My time is my time. If I spend tons of it fixing/restoring/driving/negotiating to get a great deal, then it's time well spent for me. I've gotten some insane deals in my life because I've asked for them. I've also been accused of low-balling. I don't deny it. In fact, I declare it up front. For example:
"I know it's a lowball offer, but I can offer you (lowball amount) for your (thingamajig). You might be able to get more from someone else, but I can assure you, I don't play games, I don't send endless emails asking for more pictures, re-schedule appointments, ask more questions, and be a general pain in the ass about it. If you want your (thingamajig) gone now, I will be there with cash in hand, no haggling. Easy for you. Let me know. Thanks!"
I can't tell you how many times this approach has gotten through to the folks who are just trying to get rid of an item without headaches. Let's face it: the sellers who are savvy about their pins and vids, they KNOW what their machines are worth, and they're willing to wait for the right money for them. This approach is NOT going to work on them. Period. For the un-learned seller who just wants this "big eyesore" gone, they're ALL ABOUT making it as quick and painless as possible.
But you gotta be quick. Several times I've been loading up an item and the seller has gotten calls while I'm loading it where they've had to turn down (better money from) someone else. You gotta shoot first, ask questions later.
I have gotten burned a few times too - gotten the call while on the road - it's the seller telling me he's taken a higher offer and is rescinding his agreement. It comes with the territory. I don't sweat it. Like I said, time well spent.
You HAVE to remove the emotions from this. It's business deals, pure and simple. If the buyer offers and the seller agrees, who cares what the price is? The deal is made and both parties are happy. If there's remorse afterwords, the only one to blame is themselves.
My great grandfather always had a lot of money. He didn't have a very good job and he had 12 kids with dozens of grand and great-grandkids, and his wife didn't work. Many years ago, when I asked him how he was able to make so much out of so little, his words stuck with me: "Kid, don't pay a penny more than you need to. You can ask, they can say no.