If you insist on going with something new i would strongly suggest spending more than $100, the quality really jumps after that just my opinion though
I can agree with this insofar if you include "appearance" as part of quality.
In all actuality you can get a pipe that will smoke great and last you your life (properly cared for) for less than $50:
One of my favorite pipes is my $32 Doc Grabow Royalton
That Erik Nording "FS" was an estate pipe in great condition for $42 on ebay
And the pearwood root sitter was carved by some unnamed craftsman in the Ukraine, and went for under $30 on ebay
I did put new stems on the Nording and the Pearwood sitter, but stems are found online for less than $5.
Now this doesn't mean that if I had stacks of benjamins falling out of my pockets, that I wouldn't be buying custom pipes from some of the particularly talented artisan pipe makers out there ... I totally would, because they're amazing. But I'd be willing to bet none of them would smoke better than my Doc Grabow Royalton bent rhodesian.