Well, as the name suggest, override settings override other settings. Which would explain it being placed last in the list.
How I have solved sharing common settings, is simply to put all global settings in override/.ini, and then place site-specific settings in the siteaccess folder. That way you shouldn't have to replicate anything.
That said, I can understand what you mean, and it would be nice. The only way I can think of to do that right now, is to place your "default" values in settings/site.ini, and place more specialized values in the settings/siteaccess/ folders, leaving override/site.ini.append empty regarding these values. But modifying the "original" site.ini isn't a good solution in my eyes, so...
But what I feel is missing is an additionnal level of override. When you have 2 siteaccess, a user one and an admin one, the current system is perfect.
But when you have several user siteaccess, you can not use the global override for everything... for instance RequireUserLogin, SiteDesign, etc. They will be similar for every user siteaccess, but different for the admin one, so you can't use the global override files for those.
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