This is a repost on another issue, better isolated this time. In my environment.rb file I changed this line:
config.time_zone = \'UTC\'
to this
-- This answer is copied from my original post here.
Finally solved! After posting a third question and with help of trptcolin, I could confirm a working solution.
The problem: I was using require to include models from within Table-less models (classes that are in app/models but do not extend ActiveRecord::Base). For example, I had a class FilterCategory that performed require 'category'. This messed up with Rails' class caching.
I had to use require in the first place since lines such as Category.find :all failed.
The solution (credit goes to trptcolin): replace Category.find :all with ::Category.find :all. This works without the need to explicitly require any model, and therefore doesn't cause any class caching problems.
The "stack too deep" problem also goes away when using config.active_record.default_timezone = :utc