I'm so glad you had a good time ^^.
1. The colors have a loose meaning, usually indicating tone, but it's not super strict and there's no points specifically associated with each color. So you won't always get the same results if you always pick the same color.
2. Shiloh in OL is indeed the same person from XOXO Droplets! And so in Jeremy in Step 2. We like having cameos, haha.
Thank you for the kind words <3