I skimmed through the pages here quickly, so I am not sure if any of these are mentioned.
For your first objective, Here's a couple that are definitely more expensive, but I think are actually worth the coin:
Old Forester Birthday Bourbon - I've tried a few different "birthdays", and they have all been exceptional.
Blood Oath - I've personally tried both Pacts 5, 6, and 8. All of them were fantastic.
For everyday chuckin' down your neck :
Fighting Cock - cheap as dirt, but I personally think it drinks way above it's price.
Wild Turkey Longbranch
MB Roland Straight - If you are feelin fat in the wallet, get the Single Barrel
Belle Meade Reserve
Belle Meade XO - if you don't mind a little Cognac note. I dig it.
James E. Pepper's "Old Pepper" Single Barrel. It's a rye, but I think it's also worth mentioning since it's so freakin good.
And just because it drinks like a bourbon due to the barrels they use, Slane Irish Whiskey.
I could go on.. I live in such close proximity to the bourbon trail (only an hour away from Bardstown) that I've done the distillery crawl more times than I'd like to admit.