It doesn't work yet for private messages, but we have a bug open for that! (PMs are handled differently in the code, etc.)
Our payment processor does theoretically support automatic billing, but we haven't done the work to implement it yet -- if we don't design the implementation carefully we can trigger various recordkeeping requirements around credit card processing, and it's *really* easy for a site to set up automatic billing in a way that either a) is scummy and user-hostile about making it clear about what's going on so people wind up signed up for automatic billing without intending to or b) increases the number of support inquiries around billing. (The former increases the likelihood of chargebacks, and too many chargebacks are bad for business; the latter means having to spend more time providing billing support, and since that's basically me and Jen, both of whom have a lot of other stuff going on, too much of an increase can be an issue.) It's on The List, we just haven't had the chance to do it yet.
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Our payment processor does theoretically support automatic billing, but we haven't done the work to implement it yet -- if we don't design the implementation carefully we can trigger various recordkeeping requirements around credit card processing, and it's *really* easy for a site to set up automatic billing in a way that either a) is scummy and user-hostile about making it clear about what's going on so people wind up signed up for automatic billing without intending to or b) increases the number of support inquiries around billing. (The former increases the likelihood of chargebacks, and too many chargebacks are bad for business; the latter means having to spend more time providing billing support, and since that's basically me and Jen, both of whom have a lot of other stuff going on, too much of an increase can be an issue.) It's on The List, we just haven't had the chance to do it yet.