I plugged multiple dates for Nov and Dec into Hotwire and Kayak. They all came up with 266 dollar options but not on CapeAir. In the past I was able to book directly in the American website for about that price. For those same dates I see 700 round trip. 379 to fly round trip US to SJU and then 700 for the last 120 miles on American. Booking directly with Cape Air was high 400 range. Not that long ago the standard round trip was about 180 on Cape Air.
As far as the passes you can purchase a 10 coupon book for 2000.00. They are valid for 1 year from the date of purchase and you can list 5 people eligible to use the passes. No booking restrictions and they can be canceled or rebooked up to 24 hours prior with no penalties that I saw.