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So I wanted to throw out a little tip for anyone playing, 

Place 'Go to Bar' in Wednesday and Friday. You'll note that if you don't have any of the traits unlocked, the go to bar W and F set up will get you really far without the stress penalties. Just switch the days off if you make it past the vacation time.

I've managed almost all endings, and getting 150 in all the skills (minus stress but that's out of a 100) and still manage maxing out the main skill needed, and trust for the bachelor involved.