Well, I'm certain the first route I did was Emi... and I saved Rin for last, because I assumed it would be the most difficult...
To be honest I don't remember the order exactly, but according to the dates of my review threads, it was
1. Emi (Dec 4th, 2011)
2. Shizune (Dec 7th, 2011)
3. Hanako (Dec 10th, 2011)
4. Lilly (Dec 12th, 2011)
5. Rin (Dec 20th, 2011)
Seems my assumption was correct since apparently it took me more than twice as long to finish her path than the others...
Oh and I'm not sure if I managed in every case, but I generally tried to get the bad ending first, so I could end the path on a happy note

I only remember that I apparently didn't get Lilly's bad end until much later when I noticed that I was missing the 100% graphic.