I took a look at the whole code and here is my only finding so far (I also got my tester on the case, just in case I missed anything, more on that when I have an update.) is a typo in the task reminders making it so shaving requirements aren't shown when they are added to the list. If you could send me a save file, that would be greatly appreciated, alongside which version you are playing on. If you are still on 0.4.3a, you can try a fresh save on 0.4.3b, otherwise -I know this stinks- you will have to wait until next version for a fix.
Edit: The issue is really dumb and I am glad to say it was finally found. An issue with the check means it starts from the internship instead of the first day of work. I'll be patching it for next version. For those that want to patch the file themselves, you can edit this code:
Code:
<<if $time.days % 7 < 2 && $flags.jobs.holt.active>>
to
Code:
<<if $time.days % 7 !== 6 && $time.days % 7 !== 0 && $time.days >= 57 && $flags.jobs.holt.active>>
You can do a search and replace on the file in Twine to switch it up (I don't recommend modifying your game file as I'm not responsible for the game after alterations per policy, but this is safe code that I can confirm will work).