Definitely love the idea, it brings up some interesting implementation questions... but I think if done right it could be phenomenal in more ways than one!

Resteeming with your own commentary as part of the post displayed in your blog feed seems to me like it would need to create a whole new post, with the resteemed content essentially embedded. If this is the case, then you could be paid for your resteem, or more aptly, for your resteem comment - just like you can be paid for any comment.

But what about the original content? Steemit of course has the one week limitation on voting generating content payout. What if "resteem with comment" could be a sort of workaround to keep content alive?

Imagine the "resteem with comment" feature automatically created a post with a predefined rewards split that gives 60% (possibly more, less, or user adjustable with a set minimum) of the "resteem with comment" post rewards to the author of the resteemed content.

I could be wrong, but it seems like this could be easily implementable, and allow authors to earn on their content for years to come as it is discovered and shared by the community.