You've got me! GOB is praised for it's higher ratio of content to ads, more old school publication values, that in the end - up the cost per page. Loyal readers expect to pay more per page/photo/word. They don't complain $ as the old model battles it out in the subscription rate war.
On the other hand there are a few publications(mostly local to my area-cheap paper and glossy) that, these days; are free pick ups or subscription paid for delivery to your home-only. They have a price on them $5.95(?), but I don't see them for sale. The monthly issues are in hand out stacks-shelves, at businesses, and they seem to be doing ok. Full of ads, same as CW and SAIL.
These "free" issues are financed through advertising(just like CW and Sail) but they don't depend on monthly or per issue costs, apparently.
I think someone in the sailing publication world should jump above the fray and go high end. If it had the sailing content that interests me(you can't cater to everyone), I'd give that publication a try.