First of all I applaud Jeremy for his vision and enterprise. Congratulations on what I consider to be the finest website ever.
As a currently non-paying (non-charter) member I have a few minor concerns about the new pay-to-play system.
It creates a dividing line in the geocaching community. The elite and the petite, the haves and the have-nots, the feudal lords and the lowly serfs. You can already see the line forming. In these forums people are voicing their opinions long and loud.
Will I pay? What are my benefits if I do? I get to hunt member-only caches. How many member-only caches are there? I just read a post by a charter-member stating that he will not create member-only caches because he wants as wide an audience as possible. Is this the typical charter-member attitude? I don't know. I can only speak for myself. I know that if/when I fork out my moolah I'm going to convert all my caches to member-only. I will prefer to hunt member-only caches over "regular" caches.
Basically what I'm saying is what good is the charter-membership unless you use it to it's full advantage. I'm betting that the pool of high-quality free caches will dwindle. Why would you pay for a membership and then keep on placing free non-member caches? You could do that without paying. Why post a free cache that could potentially be vandalized when you could post a member-only cache that only paying-members will be able to hunt? Do you see what I'm saying?
All of the sudden there are two classes of geocachers. The ones who pay will create pay caches and hunt pay caches. The pay caches will be as vandal-proof as they can be, they will be high-quality since only charter members will visit them. Free caches will be visible to any dill-hole who frequents geocaching.com. Any moron with a GPS can hunt one. Cache quality may start high but will inevitably decline as more and more first-timers with their McToy toting kids find them. So, what incentive does a charter-member have for placing any kind of cache other than a member-only cache? Only the assurance that more people can visit the cache. Is that a good thing?