I gave away 60-70 watches from my Soviet Era and G-Shock collection and only have a few left. The money didn't mean anything to me and it was more valuable to see the reaction of the people I gave them to. The people who did and did not appreciate it were easy to tell apart.
Too easy sometime. I gave a girl a Limited Edition Adult Swim Dethklok G-Shock and she sold it to buy booze before the day was over.
I'm the same way. Usually with guitars, but it's also been that way with headphones.
I prefer to give something away, and/or give a MASSIVE discount to someone that I know will appreciate the item versus someone that I can see is just going to flip it.
Good Moment: I went to Vietnam, and the hotel in Da Nang had a Filipino band playing there. One of my co-workers made me go up on stage and play "Enter Sandman". The guy's guitar was almost unplayable. When I got back home, I bought a red wine flame top Epiphone Les Paul, switched out the pickups and rewired the internals. It was a very well-honed, capable machine.
When I went BACK to the hotel a couple months later, I gave the guitarist that guitar as a gift. He was so grateful. He later e-mailed me and said that he gave his old guitar to his church. WIN/WIN!
Bad Moment: I had an Ibanez JS-100 guitar (Joe Satriani model). On the 21st fret is a nameplate that was supposed to say "Joe Satriani", but it said "Steve Vai" instead. I thought that was a curious oddity, so I bought the guitar. I met Joe at a Guitar Center in Seattle, and he signed it.
When I lost my job, I had to sell it on eBay. The dude that picked it up barely even looked at it, and I was saying "It has great action, try it out." He said "I believe you" and just packed it up and put it in his car. I saw it for sale on eBay the next day.
I would rather have given that for free to someone than just sell it to a jerk that doesn't care about anything but some dollars.
Then there was the time where I gave about $2500 worth of headphones to a friend that liked music, and made no money. When he got the box, he thought he was just getting one set of headphones, not 5. He took a pic of the 24" x 18" x 8" box and was like "WOAHHH! What is THIS?!" haha
One of the headphones I gave him was the Hifiman HE560. It broke. He contacted Hifiman, and they gave him a newer version/release. For free. They are now his absolute, all-time favorite headphones.
THAT kind of stuff makes me happy inside.