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“roll your own recurring billing in your rails app with a cron job, a date field for when they are paid through, and amount each person is paying”
I just saw this entry here in SO and wonder if Automated Recurring Billing is really automated. Do I have to create a script that checks if it is already the right time to bill someone, bill them and then record transactions…or should I let the payment gateway do that?
It depends on the payment gateway you are using and if they support repeat billing. If you need it, then I suggest you find one that does, rather than deal with the issue of storing billing (esp. credit card) details.