Here's the deal. The only way to effectively monetize this commercially and satisfy your kiwi needs is to have two versions (a moderated more family-friendly version and the raw, uncensored version).
The main advantage for the moderated version is that it would not rely solely on the userbase to generate income. In addition, the publicity generated on sites such as Red Bubble would naturally draw more traffic to the site. The drawback is that you will have to accept some restrictions on the use of language/content that is perceived as racist.
As for the raw uncensored version, the main drawback is that we are pretty much restricted to private donations or private sales as I mentioned above. However, you don't have to worry about restrictions on the use of content such as the N-word. Personally, I don't think we have the userbase for private sales but if you want to look into donations by bitcoin or whatever, I have no objections to putting this on the page..