You are one of those rare people qualified to comment on a direct comparison of Wolfman and the ATT Windsor. Care to comment?Everyone, of course, draws the line at their personal comfort level. For some the size of the wallet factors in, and for others it's just personal comfort. There is no question that the law of diminishing returns is a real thing. While you might come close (might) to doubling your quality from a $20 razor to a $40 razor, you most definitely will not going from $200 to $400.
I think there are (at least) two questions to answer before pulling the trigger on a purchase.
1. Can I feel the increase in quality?
2. If yes, do I think it's worth the increase in price?
I have some nice razors, but for the past 6 years I've been using a Wolfman virtually every day I'm home. I got good shaves from the other razors, but I get slightly better shaves from the Wolfman. As I recall, I paid $155 USD as James was just getting started. Would I pay three times that amount today not knowing how good it was? Probably not.
The ATT Windsor is one of the few purchases I've made that actually delivers more value for the money than anyone has a right to expect. I have one as my travel razor and consider it the bargain of the century.
Aside from that, I have found precious few products that don't offer considerably more at much higher prices. Shoes, pens, cars, houses, guitars, etc. Some will insist you're only paying for the name. Well, where do you think that name got it's juice? From providing consistently higher quality products.
I spent my working life saving for retirement, and I'm often not comfortable with spending what I consider very large sums of money for quality I can live without, but I don't deny it's there. I drive a nice car. It doesn't corner (or accelerate) like a Lamborghini, but it turns out I can live nicely without those advantages.
So I think everyone should buy what makes them happy, and find daily joy using your choices. You can only spend it once, so decide where a splurge would bring the most joy.