I made some mistakes like forgetting one festival on the second summer due to nervousness and also I really thought 17 pineapples was doable, but it isn't, you need 18 pineapples.

I found that using one sprite is slightly faster than two, and if you plan on running this category, (the WR can get to less than 1h 12min for sure) I recommend finding a way to skip the rick cutscene right when you are going to propose. And to sleep every sunday, there's enough free days later (when you sleep waiting for birthday at the end) where you can give the extra pineapple