Jay,
I really do like the Ocean Course, a great deal actually. I appreciate the architecture a great bit out there. The course has several standout holes, and a few that are superior to any individual hole at Leatherstocking. However, I think the routing at the Ocean Course is a bit strangle, especially with the 600-yard walk between 9 and 10 and the first tee so far away from the clubhouse. Furthermore, the Ocean Course always felt a bit disconnected, like the sum of the parts were greater than the whole. Leatherstocking is the opposite, with a very cool routing and intimate feeling throughout. I like the Ocean Course a lot, but the fact that I like Leatherstocking better just shows how much I like Leatherstocking.
Also $80 at twilight at Leathestocking is much better than $350 at The Ocean Course.
As for the trees at Leatherstocking, you are definitely correct. It needs some chainsawing. However, that pretty much goes for every course in this region, and Leatherstocking has plenty of other things go for it where the player can (almost) ignore the trees.
The island tee was built in the early twenties. I found an article somewhere saying it was built on junked automobiles and cement blocks. It is pretty wild to look at while standing on it, and I think it is just one of many cool, quirky features on the course.