Here's my strand in walnut. It's actually slightly darker in person. If there's a pair of AE shoes you must own then it has to be either the Walnut Strand/Merlot MaCallister.
Note that Bourbon calf is actually dyed walnut calf but burnished with black polish by AE workers.
Those who use Renovatuer will see some black polish coming off of their Bourbon calf shoes.
As such, you can actually condition your walnut shoes to bourbon by polishing it with black polish. I think people in Styleforum has rocked the Walnut Strands with Navy and Grey pants.
As for when to buy. Generally they don't discount much for Strands so if first goes for around USD295 during their Discover American sale last Oct. Seconds also aren't cheap at around USD200++
You should look out for their OEM Brook Brothers Strand which is often going at USD150 during their closeout sale. The only difference is the sole and the different insole.
Have fun hunting