Hi. Any clue the best way to exchange files with a PC?

I have a problem. I am the only Mac based system in the company. I am overworked and I need to hand off some production work. Most of my packaging is done in illustrator. I am having trouble with fonts. I have used the font converter "Transtype Pro" so that I can share files with the PC based assistant. This has had mixed results, some fonts don't show up in the menu. I had her try the "Suitcase" for windows demo but it crashes her computer. She isn't savvy about fonts or trouble shooting and IT would be mad that I even installed unauthorized software on her computer. How can I get these fonts to work cross platform?