(While I don't have any experience with OpenType, you should look at this as an option. This may produce different kerning and lines of text may wrap differently. While you may have "Arial" on both your Mac and Windows systems, they may not be identical versions the metrics for each version may be different because they're from different foundaries or they were produced at different times.
I can say with a reasonable amount of confidence that fonts will probably be your biggest issue. Adobe's website would be an excellent place to continue your research. Probably your questions are better answered in an Illustrator forum rather than here in a Mac/Windows forum.
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