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Using a content management system is very beneficial. I used to use static HTML pages and manually update everything on the site. However with CMS you can keep your site dynamic with much less effort and even (depending on the script) set the site on auto-pilot with scheduled updates.
As far as billing goes you should have multiple re-tries on any failed transaction, and cascading billing in the event that processor 1 times out or for some reason does not get the approval.
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