I think a couple of things that are easy to underestimate when one is just starting to build a bespoke wardrobe is the improvement of fit over time and even subtle stylistic changes that can throw a wrench into your plans. For example each suit I have commissioned has gotten a little bit better, this leads to me not caring as much for my older garments. Sure when I first got them, I'm hootin' and hollerin' that it's the bee's knees and fit and feel cannot be surpassed. Then you get the next one and realize that your previous suit had some tug, or pull, or rub somewhere that you never felt before because you now don't feel it in the new suit. If you are a nut job like me this makes me hate wearing that first suit now. Sure this tapers off after a while, but it translates into stylistic things as well. I went from flat front pants to forward pleats. Now I prefer forward pleats, but have all of these flat front suits in my closet. Next, I wanted to try raising the rise, wow! This is insanely comfortable and looks great, well I have 20 other suits that don't feel this great and now I want to replace all of them! It is an evolution process and cannot simply boil down to a list of colors of suits that you plan to get and dollar values that must be saved to buy them. Let me tell you, it doesn't end.
Yours must be a frustrating existence.