Well, we haven't been to a black tie event in a couple of years. She would definitely very much like to start, and I think I can probably swing invitations to gala charity function type events a couple of times a year.
She did originally make this offer when I was thinking of wearing a suit for the wedding. For various reasons I decided I should go black tie, and I started looking at OTR pretty much for the reason you're getting at, and then I started thinking about MTM.
She brought up the bespoke idea again, specifically for the tuxedo, and although I protested that it won't get enough use to justify the extra expense, she wants me to have something I feel great about for the wedding. My personal preference would be to find something a lot cheaper that I feel great about. But if it is true that a $3000 bespoke suit will really feel different to me then I understand the reasons for it.
I normally drink $12 bottles of wine, and will sometimes splurge for a highly recommended $25 bottle and they really are much better. But a few times I have had a much much higher grade (and price) of wine, and I really do get why people will spend hundreds of dollars for something they will consume in a single evening. There is a level of specialness that I have never encountered even in excellent $25 bottles that really are very very good. It's an experience that sticks in a way that "Hey that tasted super super good" doesn't really capture.
I don't know clothes very well, but I do believe it is possible that there is a similar phenomenon in tailoring, where you go -- Oh man, I never new I could feel this good about the way I look. I am just too ignorant to know (a) if it really does exist, or (b) how to go about seeking it. I won't be willing to waste her money on a $3000 tux if it's not something I believe could be on that level.