In my experience the vast majority of cheap knives can’t hold an edge at all. The super budget stainless used is just too soft. At the same time I can find many in the $70-100 range that do considerably better in that regard - I sharpen them 3-4 times less frequently.
I prefer to spend a little more on the 1-2 that get the most use.
More expensive bourbon tends to be more interesting but not necessarily more pleasant to drink. In my case it quickly becomes too fancy for my taste buds around 2-3x the price of the cheapest one. Whiskey is a bit more complicated.