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Ok, so I can confirm with 100% certainty now that yes, the PayPal button will appear for ads being relisted, even if they paid only for the featured ad ;)

http://i.imgur.com/StmiP.jpg

@danjo,...

I am not using version 3.0.5 but will surely post here if i found something.

The ad relist options should be based on the original conditions of the ad, so I would think that yes they "should" see a PayPal relist option to run it as a featured ad again. To be sure though, I...

I don't know, i am using Classipress 3.0.4

Go to your ClassiPress "Settings" page and "Advanced" tab. Then change the "Ad Box Right Side" drop-down to "Normal Full Width". Let us know if this fixes your problem...