You can get some nice buys in the under $50 links at Pipes and Cigars and Cup o Joes. One man's "arm and leg" are different from another's, and I don't know your budget, but I think a decent briar in your rotation is a must - just my opinion. I have a Savinelli Florence that I paid $35 or so for, and it is a great pipe. Cobs are great too of course.
I have lately thought Lane Ltd HGL would be a nice starter smoke. I can't make the stuff bite me, and it is has a nice flavor and aroma. It is not expensive.