As a result of reading through each of the comments I have come to some revelations and they are as follows:
Rather than run the risk of having used gear for sale always stretch to the highest quality you can afford to avoid the costly upgrade cycle. And maybe you'll keep the component until death do you part.
Avoid buying used gear to avoid the constant thinking where u wonder if it would have sounded better if u bought it new.
If I trade in used gear I will likely stretch my budget to buy something even better.
Maybe I keep the gear and eventually have enough to set up a third listening room that I will never use but it will look nice.
Finally, Selling or trading in used gear Will serve too only reinforce that u lost a lot of money on gear that you didn't have for very long. Better to store it away to forget about it or give it to a family member who otherwise would never spend crazy money on audio gear, and Hoping they don't talk to you about audio gear whenever you get together and avoid the insanity of wanting better gear and spending a ton of money.