Ben88,
That's an interesting dilemma.
The price point for high-end pipes and most artisan made pipes keep me out of the game. While I could occasionally afford such an investment, I use my pipes and I work them pretty hard. Honestly, I don't want a pipe that is so valuable that I am afraid to smoke it for fear of damaging it and that is the deal breaker for me.
As with many things, paying extra for a marquee isn't always the best investment. I am a firm believer that you get what you pay for and these days that's not nearly as much as it once was with Dunhill and some other high-end brands. That said, I would go for the commissioned pipe over the "high-end" pipe every time. With a commission, you get the exact pipe you want for money you feel is appropriate and that, to me, is the deal maker. In fact, I own a fair number of Boswell's pipes for that exact reason.
Cheers,
Chili