I think this may be skin related.
It isn't skin related it is intro video related.
If I disable the intro video the update works fine with the same skin.
The reason you have had no issues is because you do not use the intro video.
Without changing skin, if I prevent the network from connecting until after the intro video has completed, the auto update works as expected.
OR
Again, without changing skin, if I go to LE settings and click on the auto setting this starts the update check again and the update works.
So nothing to do with the skin, most probably to do with the fact that the update check is timing out while the intro is playing.
Since we can't alter when the start-up video plays (it'd be a bit pointless playing any later than at start-up), the next simplest thing to do would be delay the update check but, as has already been mentioned that's a bit above my station and not on the list of priorities for kszaq.
I had a similar situation years ago with an original G-Box that didn't have a 'wait for network' option and always missed the time update. Not being a dev myself, it took me weeks of trial and error to come up with a start-up script that waited a few seconds to take eth0 down and up again but, sadly I deleted that years back.
I'll keep slugging away at it but if anyone can save my pain, I'd appreciate it. In the meantime, it's quicker for me to update the four boxes I have manually from one download than it is to wait for the auto-update to kick in so no real loss, it would just be nice to see the notification of a new update
EDIT
It makes no difference which skin is bein used, same result.
Intro enabled = no notification / update OR Intro disabled = notification / update works