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For typical 1L books, how necessary is the latest edition? Since there are no used books they would each run $200 or so. I have access to the 2014 editions for free. How big of a mistake would it be to use the old ones?

Would be fine. Law isn't changing really and any cases not included you could just print from the Internet.

For 1L, buy the newest version. After that it doesn't matter

If you're paying 50k a year, an extra 600 or so is nothing. Don't skimp on the only important year of school