I can't make you spend $300 on one bottle, you're not paying for flavor at that point.
But here's what's very good and isn't cheap, to me. If you want cheaper stuff that tastes great, well that's a different list.
1) Woodford Double Oaked (waaaaay better than the regular stuff)
2) If you can find a bottle of Michter's Toasted you could spend some real money. This is one of the best in the last 10 years IMHO. It came out of nowhere, I drank mine in 3 days, and thought the secret was all mine :(
3) Weller 107 (lots of this around, just have to look, many small single barrel bottlings for stores)
4) WL Weller 12, if you can find it, spendy, holy shit it's good.
I wouldn't do a bourbon of the month club. Seems like shit of the month to me. These (there are others) show that you at least took the time to figure it out.