My parents pledged to a charity today and had to set up automated withdrawals with their bank account.  This got me thinking - automated deposits are trivial with bitcoin, but automated withdrawals are (by design) not really possible, except by giving away your private key.  (I'm not sure what sorts of security measures are in place with automated withdrawals from ordinary bank accounts.  It may not be anything more than the reputation of the withdrawer, and the force of the law, i.e. no better than giving away your key.)

Anyway, I was thinking that in lieu of literal automated withdrawals, a system like the following could be really useful once bitcoin comes to be used for loans, rent, payment plans, and charitable pledges: the payer can set up automated payments, and the program, so long as it is active, "phones home" to the receiver to report that the payment is in place.  That way the receiver knows if they don't receive their payment that the payer hasn't simply forgotten to send it, but is either NSF (which could be easily determined beforehand by looking at the blocks) or deliberately scamming them.

Is this something that would give lenders a little bit more of a sense of security and legitimacy in their transactions?  Is there a way this could be set up such that when the program reports to the receiver that the payment is in place, this could be trusted and "unspoofable"?

You can indeed do that!  And so I'm asking, if I (or someone else) were to write this code, would it be worth it?  And what might be the best way to go about it?