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I'm developing a site now where I plan on using Showcase as a rating area for local businesses. For now, I will allow this for free as I'm just starting up but, in time, I could see this as a money-maker if it becomes something which grows big.

I could always handle it like advertising and charge per month, etc. but it would be nice if PayPal was somehow tied to each entry.
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Opened for discussion to let others weigh in. Not even sure if this is even possible without effecting the addon (which if it does, its not happening).

How do you expect this to work? Walk me through step by step A-Z keeping the existing functionality of the addon in mind.
Well, I am here just now to purchase Showcase so I am not as familiar with the existing functionality as I will in a few days. ;)

Maybe I should play around with it and get back here with some experience under my belt.
After spending some time with it, I would think that the easiest way to handle it would be for a PayPal window to pop up once someone submits an entry. The entry stays in the moderation area for approval until payment is verified via email.
Need a bit more detail than that. How does the system know to charge that person? I need details from both the Administrative side (options, functionality etc) as well as frontend details.
I'm out of my area now, Bob. I probably can't give you much more but let me try.

I know I can embed a PayPal button which is linked to my order form on PayPal. Members have to click that button which takes them to the PayPal which, in turn, takes them back to the open form once they paid so they can click "submit". All the admin would need to do is set his ad price and enter this PayPal info into the admin side of things.

Easy for me to say because I have no idea how involved such a beast would be to make. Maybe it can be done through the User Group promotions?
TBH, what you are trying to achieve sounds like it would be better suited to Tennants Business Directory add-on.

I have this set up so that people need to have a paid subscription on my site to be a trader, and only people in the trader group and post their business listing in there.

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