I'm a hardcore bourbon drinker that had a real hard time finding scotch I could enjoy. But eventually found Springbank. I prefer the 12 year old to the other age statements and it fits in your budget.

That said, drink a bunch of cheap whiskey. Basically all American whiskey can be found in cheap expressions that capture the things that you like. Learning that you prefer Wild Turkey to Four Roses (for instance) gives you information to move up the price board.