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I have sold some that I don't regret. Before I could afford quality guns I had cheap ones. I don't regret selling my Star Firestar in .45 (but I do kind of miss the Star 9mm), or the AMT back-up in .45 (ouch), or the rossi revolver.

There are many I do regret selling:
Ruger Super Blackhawk, 7 1/2", .44 mag
Ruger SP101
Sig 228
Sig 232
Sig 245
MAk 90/AK 47 (now that you can put a real AK stock on them)
S&W 637 w/ action job

What I also regret are the ones I passed on
I had a roomate once who was sort of dumb. He used to buy guns, keep them for a while, then sell them...cheap. I never bought one from him, but could have gotten:

An Uzi Model b with long and short barrel for $700
a Spas 12 shotgun for $400 (this was about 1990) (this one hurts the most...if only I could go back in time) :-( [after thinking about it some more I think he may have offered it to me for $400---big ouch!]
a S&W 686 6" with beautiful trigger for $250