Having rigurously tested this method for probably like 40-50 hours of playtime at this point I haven't encountered a bug with it specifically once. (Can't really speak for edge cases etc. though. 🤷♂️)
And that's me talking as a professional tester with over 15y experience.
Most of the issues there were with doing the same thing over and over were you encountering other bugs in locations more often. Most of which have been fixed at this point. I could also just be avoiding the bugs unconsciously at this point tbh. Not ruling that out.
But sure, it's not intended and use at your own risk.
It's just too damn convenient to do 3x bike race in the same day, do all 3 Tristans and get heavenly husband, do 3x depression talk in the same day and not have to wait up to 10 days for her to be drinking again etc. The 'do this on only monday' stuff reaaaaally slows you down, especially if it randomly rains now (or snows) and you just lose another week of progress on it. Nobody really likes dealing with bloat. It's fine for the first playthrough. Or the first few. But not when it's the 6th time playing through 😅 (or the 20th 😛)