Most of my regrets are software related.
I bought too many LP's that were doubles (MFSL) or just any MFSL that came into the stores where i used to shop around 1990 eventhough I didnt care for the music. I know they have some slight value above what I paid (about $10-$13 each), but I just dont have the time and inclination to sell them on ebay.
And the two titles I wished I had bought copies of I recently found on ebay or here for less than $100 each (RLJ Pop Pop Alto and Athena Rahmaninoff)
ALso wished I had bought some more UHQr;s and wish I didn't sell my almost unplayed Sinatra MFSL box set for less than $300 after I realized I wasn't a gig Frank fan)
As far as gear, my evolution has been pretty good, and no real wrong turns. except I have not seemed to sell all of my previous gear when I upgraded over the last 2 years. Have to list it here and be prepared to get what I can.
One another note though, I have some gear from very small little known manufacturers (like Source technology Speakers) that are excellent but hard to sell since they are not known.
I am still tempted by these deals of amazing sound quality for spectacular prices, (often factory direct) but again they will be hard to sell when the times comes (unless of course the company really takes off and become an audiophile staple). I will never again think of a Wilson buyer as making a mistake, as those can be sold in a heartbeat.
I am seriously thinking about buying a new speaker line because it represents an outstanding value, but of course will someday be facing a similar dilmena as my Source Tech's but on a much higher financial plane.
One thing I don't regret was 16 years ago buying some used Atma-sphere MA1's. I played with them on and off over the years, always being tempted back to solid state if many tubes blew out at once, but eventually I retubed them and found they sounded better than SS. I had no trouble selling those for a good price and upgrading to brand new MA1's.
So I guess well regarded tube gear is perhaps a better investment?
