I would normally not buy a coin in this condition but for $14 I was interested due to its age and the counter stamp. Is there any way of identifying the counter stamper?
That's going to be tough. Single letter stamps like these are common, but getting a solid identification just from that is likely damn near impossible. The only counterstamps involving a single letter I've seen identified are those that had a unique style or some accompanying shape, cartouche or pictorial with the letter. The S punch here appears to be of an old style, but that which would have been common for probably about 2 centuries. Best of luck