I'm just doing this very research tonight, and based on the current implementation of SDWebImage, it looks like there's no "built-in" way to use a Conditional GET (etag or date) type request to the server to check for updates.
The way I'm exploring now is to create a unique URL, so as the server version of the image updates, append either a hash or version to the end. Something like:
http://example.com/myimage.png?v=2
And increment that version number as the image changes, but keep the myimage.png name the same since that doesn't change. That should force SDWebImage to download the new image and build a new cache for the new version of the image.
Otherwise you'd have to tweak the constant value cacheMaxCacheAge
in SDImageCache.m to check more frequently than its default of 1 week.