Try this, pick 4 to 8 Bourbons with the majority being under $30 and two being something you love in a similar alcohol level. For instance at ~100 proof:
OGD BiB, EW BiB, Virgin, Early Times BiB, JTS Brown BiB, WT 101, and then an EHT SB and EHT SiB. Have someone else pour them in similar glassware and mix them up so you are unaware of which is which. Spend an hour or more trying them and then line up from the one you love to the one you hate. If you don't dislike any then just rank them. You might be surprised what comes out on top.
I have a friend, who is a homebrewer, and who is also a Whisky judge at an international competition. Despite his experience and knowledge he relegates EW BiB as a bottom shelf mixer. I don't think he has ever tried what I suggest above. I think he is making the mistake most do and not allowing he palate to make the decision.
This sounds like a fun idea for something to do with my dad. He drinks a lot of bourbon as well. I'm mainly a fan of Cedar Ridge bourbon, Woodford Reserve, and Mississippi Distillery out of LeClaire, IA. Most around around $40 a bottle, but if I buy them at Costco they're always way cheaper.
Has anyone tried the Kirkland bourbon? I've been tempted to pick up a bottle just for kicks.