I think there's a limited market that would pay for this now, you say you would, other users say they would. But this is not something he can offer to only some users as an extra feature, so all his users would have to be comfortable with it. From a business perspective, I imagine he has done testing to figure out what price is right and from a security perspective it would probably is not too unreasonable if he just waited until he had enough volume to allow this to happen with only very limited price increases or at his current margins.
In the meantime, the bug bounty + very qualified developer strategy seems like a reasonably sensible option while the service is presumably, still in its growth phase. I guess we'll find out.
Speaking as a Tarsnap user, he ought to. The service is seriously underpriced right now.