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This would work well with my FaunaClassifieds.com site, but with a twist. I would like to have the photo option determined in the user group section. In other words, I could turn this off/on via a checkbox as an option to any usergroup I choose. Since I have paid levels in my vBulletin site, it would be logical to add this as a perk to the paid memberships yet leave the non-photo ads for the free membership levels.
This also brings up another issue.
I would like to see each user able to set up a "pool" account where they could pay via PayPal a larger sum of money and each of those optional paid bells and whistles would draw money from this account. The reason for this is that PayPal takes a whack off of the top for every transaction. I am charging $1 per optional enhancement, and it stubs my toe on the fact that PayPal takes 33 cents out of that dollar, leaving me only 67 cents. I don't really want to charge less for each option, otherwise my account is just working to put money into PayPal's pockets, and not mine. So if a user could put in a larger chunk of money, then the PayPal hit won't hurt quite so bad.
Also looking from another perspective, this sort of arrangement with single charges per ad per enhancement tends to discourage high volume advertisers. $1 per hit doesn't sound too bad, but suppose you have advertisers who may want to place thousands of ads over a year's time? This will begin to get expensive for them. Sooner or later they are going to start asking about a volume discount, say like 100 options for half price or something along those lines, if they pay that amount in lump sum up front. Or perhaps as mentioned at the top of this reply, something like that could be tied to the user group level. A specified "prestigious" membership level would come with a set dollar level of bonus points that could be applied towards those paid enhancements. This would certainly encourage some people to ante up for that membership level, because they would see the benefits right off the bat for doing so. And on the bright side, it would leave much of the payment overhead up to vBulletin. vBulletin already handles this pretty well, with automatic notifications of pending expiration dates. All PP_Classifieds would have to do is to grant those special options based on the settings in the user group level.
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