If you honestly want to spend money, please spend it on upgrading the website software to current web standards. That's long overdue.
Also, your planned pricing as you have currently expressed it has the appearance of being bizantine, scheming, punative and petty minded (which is as kindly and generously as I can put it). You'd do far better by just charging a small fee for signup plus a small fee per add placement and leave it at that.
After the year is up, I'll likley continue on as a subscriber, but maybe not as a supporter. I don't wish to support a content boondoggle.