Considering the Dude needs to replace the car the nihilists burned up, how behind he is on rent by now after millionaire Lebowski welched on his 20k promise, and the high likelihood of hyperinflation causing Maude to rethink her decision to raise Lebowski Jr. on her own dime, pipes and tobacco are probably the last things on the Dude's mind. Although I do know that if he were to imbibe in the hobby, he'd pay for everything by check.
Factoring in the Dude's anemic finances, I'd guess a MM Country Gentleman and something by Lane, since he is a bowler.