I experienced scenario 1 in about 1980. I was working for one of those weekly advertising newspapers that were big at the time but couldn't still exist in the age of Craig's List. I was the circulation manager (when I was 19 years old) and I'd be the first one to see the whole paper together when I'd take the big sheets to the printer the night before and they'd run the first few and I'd have them the night before they came out.
One night I had an unreleased paper for the next day and I saw an ad for a 60's Gibson Firebird with a price of something like $50 on it, maybe it was $80, but it was waaaaay too low. I stopped by the address the next day and there was a middle aged lady who's son had been killed in a car accident a few months before and she was slowly selling off some of his stuff. It was incredibly sad. She handed me the guitar and I played it a few minutes and it was a great guitar, somewhat vintage, and it was worth a lot more than what she asked. I told her that - I said I'd like to buy it, I didn't know exactly how much it was worth, but it was worth a lot more than she was asking, at least several hundred dollars. She thanked me for telling her that and said she really didn't have the time or inclination to really look into it, but what did I think would be a low, but fair price. I told her $250 (or around that - this was a looooong time ago and i don't remember the specifics that clearly anymore) seemed like it was at least getting into the neighborhood of what a music store would probably give her for it. So she sold it to me for that. It was a great guitar - I didn't really bond with it all that much, being a strat guy. And a couple years later I sold it to a friend who really loved it for the same thing I'd paid for it.
I'm sure I still got a screaming deal on it, and I enjoyed having it, but I no way wanted to profit from that lady's pain, so I had it a while and passed it on. I gave her what I hoped was a somewhat fair price for it. And I didn't lose any sleep, but always felt funny playing that, knowing it's history.
-Ray
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