I understand what you are saying. I purchased my first Allen Edmonds almost 5 years ago. Since then i've gotten about 15 pair of AE, at least 10 Aldens, and 5 Carmina. Over half of my shoes are shell. I've probably gone overboard but that first purchase was justified by the idea that i'd be able to wear my Allen Edmonds for a long time. $350 every 10 years is better than $75 every year for shoes that will only last a season. With shoes you really do get what you pay for. I'll also say that if you can't afford them then don't get them. You can also snag some pretty decent deals on AE shoes from different places. If i'm not mistaken you can get the Lasalle right now for $129. This is a great way to get into a pair of Allen Edmonds without breaking the bank. There are people here who are wealthy but then there are people that are not. It really comes down to priorities. For a lot of us dressing in high quality shoes and clothes is a priority. For many it goes with our profession while for others they simply like looking sharp. My mom rolled her eyes wen she saw the price tag of a pair of AE (this was when they were $325). She couldn't believe that people paid that much for shoes. Her husband (not my father) regularly pays $100+ for Under Armor "officially licensed" college sports shirts. THose shirts last two years and he has to replace them. My shoes will foreseeably last 30 years. It's all in what you like.
Oh, and stay away from shell or your wife will flip.