I am both biased and spoiled, as I have a very close friend who works for Beam. I visit with him frequently and therefore I get a lot of free tastings.
There are some truly fabulous bourbons out there.
There are many excellent ones.
There are plenty of good "every day sippin" examples.
There are some real stinkers out there.
Some uber expensive bourbons are not any better than a decent $25 bottle. I've seen some folks spend upwards of $300 and not get a good return on the investment. Just because a bourbon is $$$ does not automatically mean it's worth the price of admission. Some expensive bottles are wonderful, but not all. And some inexpensive products are really quite good. Others are garbage. Typically, beauty is in the eye of the beholder, and that is as true for bourbon as it is for cars, cigars, stereo speakers, firearms, etc ...
There seems to be a law of dimishing returns on bourbon, not unlike wine, cigars, etc. Spend more and you'll get more, but the cost may not return the percentage of value. Spend $100 vs $25; are you getting a bourbon that's 4x better tasting? Not always, if at all. Most any decent bourbon will cost between $20-$50; after that, you may not really be getting the value for your dollar. I've had penty of delicious bourbons that were over $100, but they weren't THAT much better than a $45 bottle.
The bourbon industry is seeing the same explosion in "start-ups" that craft beer did a few decades ago. Just about every place wants to up their game by trying their hand in making brown juice. A few are pretty good at it, but many are just preying upon the unknowing consumer by being "novel" in their approach and presentation. I tend to stick with the established great brand marketers; Beam, Buffalo Trace, B&F, etc (and all the sub-brands they own). Beam alone has the following: Beam, Bookers, Bakers, Basil Haden, Makers Mark, Knob Creek, Ol Tub, Old Grandad, Repeal Batch, etc, etc, etc ... And many of those have their own sub-brands (BH for example comes in the standard 6 year, but also a 10 year, and a Subtle Smoke, the Toast, Dark Rye; all yummy!).
Also, I don't believe there is a "wrong" way to drink a bourbon. Some like it on the rocks, some like it with a splash of water, some like it "neat" (cut to some preferred proof). If you're happy with the way you like it, then drink it! About the only thing I find a bit offensive is when someone takes a very good bourbon and then pours it into a sugar soda (Coke for example); kind of a waste IMO - if you're going to do that, just use a base-level bourbon.
My go-to bourbon is typically Beam Black Label or Double-Oak; I can get them easily at Kroger for less than $20. Excellent hooch for the price!