Tswhitsel:
You ask how I feel about selling my gear at a 40% to 50% markdown when I upgrade? Here are a few of my thoughts on that and the other points you raise:
First, I wouldn't play the game this way if that was going to bother me. The price of going for exactly what I want (which I've had the luxury of doing for the last few years) is knowing that there will be that kick when I sell it. I simply accept that as one of the costs of playing the game by my rules.
Second, someone has to be the initial buyer of all the stuff that shows up in the classifieds. Every one of those items had one buyer who payed close to list. Thank me for being one of them - I know that the friends who have bought my half-priced amps are content to have me doing some of the heavy financial lifting, and I'm happy to have had the ownership experience. Whenever I've moved on from a piece I've always felt that the music I enjoyed while I had it, lessons I learned about audio and my own tastes, and the pleasure it has given its subsequent owner were worth the price.
On the subject of dealers:
Of course my dealer gives me good prices as well as good service. Given the coin I've dropped on him, that goes without saying. He's a friend as well, so there's no way he would jeopardize that by shaving me too close. The fact that I don't quibble when he quotes me a price means that he has really gone the extra mile when support has been required - even if it occasionally involves fixing gear I've bought elsewhere.
I don't want to leave the impression that I have depended on his ears to assemble the system as I went along. In fact It's been the opposite - I have generally told him what I wanted, or at least what sound I was after as my discrimination evolved. I've frequently bought direct or from other dealers when I wanted to experience brands or styles of equipment he doesn't carry. The few times I've had "learning experiences" were when I've done this. But my dealer's ears really are that good, and everything I've auditioned on his recommendation has found a solid home in my system with no regrets.
On markups:
I don't worry about the markup on a piece of gear. What I worry about is whether its value to me justifies the asking price. If it does then it's a good value, no matter whether the seller is making 15% or 50%. If its value to me doesn't justify its price, I walk away. I've been in the luxury position of being able to make buying decisions based on perceived value rather than simply price.
Lastly, it goes without saying that this is just how I feel comfortable doing business, given my circumstances. There are no big life lessons in here for anyone else.
