Well as far as tobacco, I personally doubt you could do much better than the Seattle Pipe Club blends! (Yes, I am a member.:)) You can get them from
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pipesandcigars.com
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Or just a good English style blend. I'd stay away from aromatics personally--they burn hot & wet, they can bite (badly), and you don't' really taste the tobacco at all. Natural blends are much more flavorful & complex once your palette adjusts & learns to pick up the subtlety.
As far as a pipe, maybe a Nording in the $80 range--their freehands are more expensive but supposedly great smokes. You can probably find one @ any good tobacconist. Or a Savinelli. Or a Peterson if you don't mind spending more.
Look up "Frank Method" for packing a pipe--ignore his recommendation to light it w/ a torch lighter, though--unless you want to destroy your pipe.:medvl: Not all tobaccos will work w/ this packing method, but many will.