Back in mid-September, I found myself at Liquor Barn just after they'd received their bi-annual Van Winkle shipment; I bought over a case of 90 Proof 10YO Rip Van Winkle (of which, I've consumed two bottles). I laid it in at $27.39/bottle; at the time, they also had 15 YO for just under $50, 20 YO for about $110, and 23 YO Pappy for right at $220. I've never tried their 15YO+, but I've been quite happy with the 10YO RVW and would heartily recommend giving it a try.
I was told that many consider the 15YO to be the best value and that it sells out quite quickly. However, I find its 107 Proof to be a bit off-putting; I tend to water down even 90 Proof, although the Van Winkle is smooth enough that I will drink it straight up occasionally.