Hey @hammertime !
Got a very similar problem with sub domains, however I do not know if it has something to do with reverse proxy or not - but my assets does not load for either plugins or themes, but all template files is correct.
First, did you come up with any solution to this issue?
@Sommerregen posted a neat snippet for setup.php in the forum and i'm using it to leverage the subdomains. But still, the assets... Djamil (@w00fz) did take a look but did not see anything...
Eg: when accessing columns.ini.onl the server looks for ini.onl/columns - and as that folder does not exist all the assets will break.
So started digging into both the setup.php and htaccess to see if i either htaccess could rewrite the path to root for subdomains - but keep the url intact, or set the $environment in setup.php to not use the sub domain.
Both ways was with no success, probably for the lack of knowledge, now it is just tearing me up. Then saw your post, now feeling like we need this solved so no one will experience this dreadful issue again.
Any help would be appreciated.