The idea is OK, but one needs to have connections in typographic community to execute it. Going foundry by foundry and convincing them to take their heads out of DRM hole and consider simpler, unsexy options such as this one. This can translate into a lot of effort.

If you are allowed to buy a font to make images for your website, why wouldn't you be allowed to sell those images to others? Professional web designers do it all the time.

(Video rentals are similar. First sale, and all that.)