This Dunhill topic has been beaten more times than all the wives and kids of players in the NFL combined. Dunhill's carry a legendary reputation in the pipe world, and deservedly so, as they are one of the oldest and most well respected brands in the world. If you want a Dunhill, get one. I own 1, a '75 root briar apple straight shape, and i pretty much bought it to see what all the hype was about and say that i own at least 1 dunhill. Would i do it again? Yes, the pipe smokes very well and it is a 40 year old piece of history. I think that is cool. Others may not. I do think Dunhill's are extremely overpriced BRAND NEW, especially with the widely discussed issues they have these days with quality control and living in the shadow of what they once were. I'd take a Castello any day of the week over a Dunhill.
Bottom line, if you have the money and think it is worth it, buy a new Dunhill. If you want to save money and get a possibly better smoking pipe, buy an older estate Dunhill. In any order, it sounds like you are set on a Dunhill and i think Dochudson is spot on in that if you do not buy the damn Dunhill, you will probably always wish you did every time you light up whatever pipe you bought instead.
Good luck on whatever you decide and let us know how it goes!