I noticed some of you guys letting go of stuff on eBay(and I bought some of it), and I was curious:

Just how agonizing is it to get rid of a really cool item? I almost brought myself to selling my Hellbound box once, but The Pain kept it from happening, and I am glad now.

how do you overcome it?

It requires a moment of clarity, when you realize you have enough invested in old sheaves of paper that you could buy a house.  Things flow quite easily after.

The Pain is doubly worse knowing all the classic AD&D stuff I foolishly traded in to used bookstores for pennies on the dollar (of the cover price!) back in the Eighties... After all "I wasn't going to play anymore" and "it was always going to be around" I told myself.

Famous Last Words.

Sometimes when I look at all the "stuff" I have acquired I wonder how much money I have laid down. . .

Then I think:  " Whatever it is, it isn't anywhere near all the cash I have wasted on overpriced meals I didn't like, clothes I never really wore, movies that cost $8.50 a ticket and still suck and all kinds of other crap that is now faded and just a hazy memory.".

Just remember the last "so-so" nice dinner you had that ran you $75.00 and put 2 lbs. on your waist.  Then go grab you R1 or Amazing Spider-Man #129 and look at it for a few minutes. . . You'll worry a whole lot less about all the money you "could have had" . . . I guarantee it.

I actually had an odd experience in 1993-1994 - I got out of RPGs entirely, trading over 300 supplements (D&D, Cthulhu, BattleTech etc.) in to two game stores in Colorado Springs.  They gave me trade value only - over several sessions, I traded everything in for my then-current addiction, Magic:  The Gathering.  I got quite a few boxes of Alpha, Beta, Arabians and Revised.  I had 12 Lotuses at one time.  I sold out to various sources in 1996, and lived off the proceeds (~$33,000) for half a year without working.

I became quite the bastard then.  Which lingered until about 2001 or so.  Work suits my spirit much better.     Fortunately, when I got bored I turned back to D&D.

I remember when people were paying $75 for a black lotus. I thought they were insane...

I am slowly dumping my entire MTG collection. They are pain to scan and sell, though. But as the mood strikes a load up 20-30 aucitons. Another one of those "coulda" "shoulda" deals. We got into the game fairly early (revised edition) but never bought too many cards. Shit, I only picked up a few Legends boosters...how is that for stupid. We played, and for ante every game, but that was it. None of us really collected. Crap.

But closer to the heart of this post. I have no problem dumping those cards.

I would have a huge problem dumping my core AD&D/D&D stuff. Most are original purchases...I bought my holy trinity for cover price when they came out! How could I possibly sell them?

There has been a rash of old-timer collectors dumping collections - Burnt is only the most recent. I would have a tough time doing the same. Of course, I am not in that class. My collection is pretty much restricted to AD&D and (Basic) D&D items published prior to the release of 2nd Edition. That makes my collection look pretty small compared to the heavy weights of collecting.

Since my collecting wasn't restricted to one particular area, I had a lot of items all over the place.  Many things I had no problem giving up.  A few things I chose to keep, simply because of what they were.  For instance, my bookshelf right now has about a tenth of the actual amount of gaming material I own.  Besides the obligatory D&D/AD&D material, which takes up just under 50% of the shelf, I have the games I absolutely refused to send to storage because of what they were. I'd be nuts if I took my copy of Dune: Chronicles of the Imperium to storage and risk having it damaged while cooped up in a plastic tote.