Once you have a reasonable rotation of decent clothes, you might as well take a chance. When bespoke goes well, it's genuinely surprising how much better it is than RTW. Odds are that it won't go well the first time but it is usually pretty good by the second go-around, assuming you pick a tailor who's got the skills and a style you like. If you know going into it that it's a long drawn out process and that you're doing it for the next 10 suits over the next X years, you won't be as bothered by a few bumps at the start. Or by the problems you'll eventually encounter even after you think everything should be going perfectly smoothly. It's a marriage not a one night stand. Marriage isn't for everyone but there's certainly something to be said for it.