I don't see anything obvious, but there are a few things you could try:
1. Change the aliases on the non-web context docs so that you don't have any resources on the site with duplicate pagetitle/alias combinations (e.g., JillsHome)
2. Don't give any resources the alias of "index"
3. Remove the two Member Context Access ACL entries (they really shouldn't have a policy of Resource since that's not a Context Access style policy -- it's a Resource Group Access Policy).
4. Turn off the compress_js and compress_css System Settings (if you haven't already).
TBH, I don't think any of that should really matter, but we're running out of options.
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