Welcome Matt!
Nice avatar! I bet that little guy can really load a pipe. This is a long post but something about your question made me feel that you deserved a long reply. So, hopefully you'll appreciate what I have written here for you and it will help you along in the adventure of hunting for the perfect smoke.
I've been researching and learning about pipes for about 2 years--this is nothing compared to most everyone else here. But like many people I have champagne taste on a beer budget. I agree wholeheartedly with Robert. Estate pipes are the way to go, especially if you want a high-grade pipe, (which I usually do) or want to get several low-to-mid grades. This way you won't break your bank. People will all tell you something different when it comes to what we all think is best in a pipe or tobacco blend. But we are all different and like different things. So, there will have to be some trial and error for yourself to some extent.
There are a lot of respectable pipe makers out there these days from the boutique hand-made pipes to the mass-produced factory-made pipes. You can spend $5.00 to $50,000.00 on a pipe. I think it's best to balance the characteristics of what you like and find them in the pipe you purchase within your budget.
Personally, I like to keep my pipe looking clean and well-kept. So, I don't tend to hold them in my teeth for a long time without holding them. Plus, I like a large bowl for long smokes, which a sizable pipe is hard to hold in the mouth freely anyway... I want the bowl to feel nice in my hand and not burn me, I want the smoke to be cool and mellow; not hot, I like the draw of the smoke through the pipe to be easy and feel regulated well. And I like the pipe to look like a piece or art. So, I end up gravitating towards middle grade pipes and upward. But this is what I like.
Just look around at what people are talking about here, look at what's for sale on ebay under estate pipes---just get ideas. Unfortunately, you don't normally get to test-drive a pipe before you buy unless you've got friends with pipes or know a cool person at a pipe shop that will work with you. SO, I'll tell you my personal favorites if you like similar characteristics in a pipe like what I described. In order of my personal favorites:
1. Ardor - my favorite brand - very nice smokers - never smoked one that was not at worst, an excellent smoker. They are mid grade or higher and so normally run $250.00 and up new.
2. Savinelli Signature
3. Radice or Bjarne Nielson
4. Stanwell - excellent for the price point here - go ahead and go for a legend series or a Nanna Ivarsson series
***Try to get whatever you can as a clean estate pipe -- my favorite trick -- talk to the guy/gal that sells the pipes at a tobacco shop and see what he personally smokes. 9 times out of 10, he'll pull out a really sweet pipe and show it to you, and everything they smoke is for sale because he/she wants to sell what they are personally smoking so they can justify buying something new. Pipe dealers are pipe-fiends and they have to constantly be buying something new. LOL. It's funny but true. They'll usually make you a great deal and they normally properly care for their pipes and have broken them in correctly.
Hope my opinion gave you some food for thought!!!