I'm having a problem where I can get the first 3 omo events but not the last 2 (in the first 5 omo time ones), the brother shows up and it ends there and I guess she doesn't have an accident? If I check the event there's on the first 3 filled in.
I am pleased to say that through an unprecedented feat of combined luck, wizardry and google-fu I have managed to find the proper font pack required to make it run on wine in a 5-year-old forum thread barely related to the topic.
Instructions:
First, you have to unpack it properly. This is a problem, as .zip isn't designed to deal with non-ASCII filenames and most .zip extractors aren't smart enough to get around that. If you're on Arch, install unzip-iconv from AUR. If you're on a different distribution, I'm afraid I can't help you and you'll have to find an equivalent, adapt the Arch package, or hope the game is reuploaded in a different format. If you have access to a Windows machine, you could extract it there with 7z and copy it over. (Windows version of 7z through Wine? Good thought, but nope, doesn't work.)
Unzip the game and try to run it, setting the appropriate locale:
$ LC_ALL=ja_JP.UTF-8 wine Game.exe
If it doesn't start with an error message with something about "Graphics/Titles", then either the unpacking went wrong or the locale wasn't set properly - if you haven't used Japanese locale previously, you may have to enable and build it. This is distribution-dependent, so you'll have to find instructions yourself.
If it starts, there will be no text. That's expected. Close it, download this font pack: http://rpgmaker.net/users/kentona/locker/Fonts.rar
and extract its contents in ~/.wine/drive_c/Windows/Fonts
After this, the game should run properly (remember to set LC_ALL). It does for me. YMMV, though.