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Isn't it annoying when you want to comment on an article, but don't want to go through the hassle of creating yet-another-user account at yet-another-website?
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We won't mind a bit.
Taking hyrcan's advice, we've added the proper rewrite rules and are set to push the website to production (we'll see if anything else comes up). After some testing, the decision was made for /node, /admin, and /user not to be effected by the rewrite rules I remember not being able to change some settings if /admin wasn't excluded, while /node was excluded due to some (potentially unrelated) file upload issues and as a just-in-case measure.
In the process of implementing the rewrites, the conf file was tweaked and re-ordered a couple of times due to conflicts with other rewrite directives. Perhaps further proof that it might make more sense to do it on the Drupal level.
As for the logic behind how it should work -- if the path appears to be a file name (i.e. .html), no forward slash should be appended. Otherwise, if it appears to be a directory - it should be treated in the same way Apache treats a directory accessed without a forward slash: it does a 301 redirect.