I share your approach and have repeatedly chosen Transparent by direct comparison. Well articulated. Particularly I have found the two cycles of withdrawal act the most telling.
I agree about assessing your system before starting. In the past I have had to make up for some shortcomings in my components because of lack of funds. But, my feeling is if your system is fatiguing, you have a serious component noise problem and it is likely much better to put money into fixing that directly. I have to agree that cables and interconnects can make a huge difference… but in a well chosen synergistic system they will only make a relatively small difference. This is why, for me, Transparent only have become the right choice as my system became much better and not in need of correction. Transparent just get out of the way. That is a good thing for my system now.