Caveat: I'm not the most experienced pipe-smoker.
I think an aluminium Falcon is a great place to start. They're not pretty pipes but they smoke amazingly well, they're cheap and you can have a single stem and multiple bowls. The benefits are that it's easy to clean, smokes cool and dry and if you hurt the bowls whilst learning it's not a huge loss.
If you're not keen on a chiefly functional pipe and really want something pretty as well, I'd recommend (as I was first recommended) Peterson. Peterson pipes don't cost the earth and there are some great styles out there. The only thing to watch for is that they put a stain inside the bowl so you have to wipe it away with alcohol before you first smoke it, unless you don't mind it tasting bad for a while.
As for repeated wisdom, I've heard that Savinelli is also another great starter brand to try. There are some truly beautiful pipes in their collection and they're supposed to be good performers.
Don't limit yourself in the design of the pipe. My taste in pipes has changed markedly. I'd see what a manufacturer has to offer and then make a decision on what you feel is right.
I hope this helps.
Leigh ~ straights, single edges, double edges, boars, badgers, pipes ~ BOTOC