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If you use vbulletin there is a way you can do this easily using the subscription feature.
1) Create a limit on the number of ads "Registered Users" can upload.
2) Create subscriptions ( say Classifieds Users, Premium Advertiser ) in vBulletin and assign new limits to those user groups in photo class.
vBulletin handles recurring subscriptions nicely and you can offer paypal and a few other payment options.
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