If you can manage it, buy a meerschaum pipe. I’ve got two that I bought years ago for about $15 each. I tried wooden pipes, but they always seemed harsh - the smoke felt like it was still burning.
I did a quick google, and it looks like you can get meerschaum pipes from about $40 up. That’s a fair price, considering that I bought mine 15 years ago in a US Army Exchange in Germany that imported them directly from Turkey.
Meerschaum smokes so much nicer than anything else I tried.
Captain Black vanilla is a nice tobacco. I also used to buy an inexpensive brand, soak it in amaretto and dry it beofre smoking. Nice flavor. The absolute best, though, was Avalon. That’s an American light tobacco that’s been soaked in French red wine. It smells good, and tastes good. It’s even nice tasting if you manage to get some of the tobacco juice in your mouth.
Gawd, those were the days. Kicked back in the NCO Club with a glass of Amaretto and milk, my eagle claw meerschaum pipe filled with Avalon, and having a good time.