Mod reposting of a wordpress site (classipress theme)

Project Description:
Hi,
I have a classipress wordpress site www . mercadobarcos.com.
This is a boat classifieds site, where users can register and publish both free and paid (featured or premium) ads.
I have attached a file with screenshots for a better understanding.

I have the following problem:
When a paid ad expires it goes into "Draft" (in wordpress) and the user can just click "repost" from their user dashboard, and the ad would go published without the need of paying for it again.
I want the "repost" link to take the user to the payment step when posting so he has to pay again in order to repost the ad.
Once he goes through the process, the ad has to go into "Pending" (wordpress) where i can activate it once I receive the payment. (this is how the actual posting process works).
So basically, i want the user to go through the payment process again in order to repost a paid ad.

These other things need to be done also:
-When the ad is on pending state, the user sees the ad in his dashboard with a "Paypal" button that takes him directly to paypal payment.(see attachment) This option appears in case the user skipped the payment part when posting.
I want to replace the paypal button with a "pay" button that takes him the the payment step.
-All ads in the user dashboard look the same, free, featured and premium. I want to put different colors and a tag, depending on which type of ad it is.

Please register and test my site.

If you have any questions please ask.