In years past, I have, in one form or another discussed this topic......... and it is still dear to my heart. My reasons for pursuing it again are that we have a new crop of bourbon drinkers joining our ranks, and because I think it is an important topic to bring up in an 'Enthusiasts' site.
Drinking bourbon is not without plenty of risks, make no mistake about that. For some folks is can only be described as poisonous, in every sense of that word. I will address few words there, other than a few cautionary ones......... do not abuse bourbon because it is stronger than you if you do. It cares not one whit for you, your family, or your friends. It should never be considered your friend for it surely is NOT, but it MAY be a charming companion.
The best thing about bourbon is that it can be consumed and enjoyed in moderation. It offers wonderfully complex tastes with great variety and it can give you a temporary opening into a world of less stress and open the door to a conviviable evening. But within always lies a beast that can consume you. It must be respected.
There is no best bourbon, never has been, never will be!! It is in the variety that one finds the greatest satisfaction.
The is also no best bourbon for the money. Like in everything else, a loose rule of thumb is that you get what you pay for. If inexpensive bourbons satisfy you, stay with them......... there is nothing compelling anyone to leave his/her comfort zone.......... although for an Enthusiast, I do not recommend that.
If money is a primary concern for you, the differences between the more expensive bourbons and the less expensive is only partly a result of real differences in quality (although there is undoubtedly some as a general rule), much of it is hype (like it is in almost everything we are offered by our marketing system). So let the buyer beware!
Always be aware that your palate is bound to change over time......... so what? Taste more bourbons, learn more about your own palate.
Do not go gentle into that good night,
Old age should burn and rage at close of day;
Rage, rage against the dying of the light. - Dylan Thomas