Yeah, I don't necessarily think you should change everything. There are many considerations. I'm going to get into some more things in my next "longer" post, about scheduling and such, and that will touch on some other things. More importantly, though, I think your audience is what you need to keep in mind more. Or in other words, I'm not your average buyer. I've played quite a few dating sims, you know. Also, I'm not a woman. I think, probably, for the casual gamer, the game should probably more easy. I think a lot of the things are going to frustrate casual gamers. I think your idea of an easy mode was a good one. I think there is a good portion of your players who would probably like to just play it, and basically win no matter what they do. So as long as an easy mode is designed with "everyone-can-win" in mind, I think that would good.
Anyway, as I said, I'll be back with thought on Scheduling, and as long as we're speaking Otome games, I'll throw in some nifty things that might make it appeal even more to girl gamers. This Tokimeki Girl's Side I played just last month really had some neat ideas for Otome games.