Did you check to see if you can load your autosave? The autosaves are locted under the A on the save/load screen. The topmost leftmost file is always the most recent one.
Because of the way stat progress is done, day 100 could mean literally anything, so the file you download may be further along or not as far along as you're hoping (and if it's past where you were, you may miss content)
I messed up with the auto save and it just didnt show up my old progresses. All i know is my progresses with some girls are:
+miku: hugging night after she was in chaos
+sana: after we tell her we might get replaced at the end of the year
+makoto:the night after she masturbate and we had some sort of date or something at 2AM
+i forgot the twintail girl name but after she showed us her parents grave
+Ayane: after we kiss her and she tell us about the marriage thingy stuff
+maya after she did some mediate or something in shrine
+futaba: after she almost confess to us in her dorm and got interuptedby our niece call
+after we met haruka
Other than that i think the lastest main event i occured was the cooking night.Had some more too but i dont mind grind them again. And yes i will definitely miss some contents but as long it isnt too many i can be fine with it.