The biggest hurdle today is the bourbon boom that has happened over the last five years, with a ton of 21 to 35 year olds deciding to get into bourbon. Nothing wrong with that, but the demand has far outweighed supply, especially on the limited release stuff. So many things have become allocated that used to just sit on the shelf. It has also created a secondary market, with absurd prices on hard to find bottles. Another problem is a bunch of folks are collecting bottles rather than drinking them.
20 years ago, I'd buy Rock Hill Farms or Blanton's for the weekend at about 45 per bottle. Now, the MSRP on those is up to 65, but you won't find them on the shelf. Rock Hill Farms no longer comes to Oklahoma. You won't see Blanton's on the shelf...if you do, it's 80 to 100. Blanton's is good, but it's not that good. I have a couple bottles that I paid 65.
So it's frustrating as a longtime bourbon drinker that now it's hard to find some things. Producers have ramped up production, so supply will be up in five to 10 years after everything has aged.
To answer your question, everyone has a different palette, so you might not like what I like. With that said, I think there are some "crowd pleasers" that are basic, but really good.
For around $30 to $40 for a 750mL, look for Knob Creek 9-year, Buffalo Trace (a little hard to find at times), and Maker's Mark Cask Strength. If you move into the $45 to $60 range, Baker's 7, 4 Roses Small Batch Select, Old Ezra 7 and John J. Bowman Single Barrel are fantastic and worth the money. If you can find them, Eagle Rare and Weller Antique are tasty in that price range. As for some budget options, Larceny, Evan Williams Bottled-in-Bond (BiB), Early Times BiB, JW Dant BiB are good options and usually come in under $25. The Evan Williams BiB can be found for $15. I'm sure I'm forgetting some good ones.