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Eurail pass or point to point tickets? Please help

Hello, I am arriving in Zurich July 8 at 6:30 PM and will be returning to New Orleans on August 18. I am trying to determine if its cheaper to get all point to point tickets or maybe a flexi eurail pass or perhaps a regional pass. Please look at the trip i planned out already:

http://www.eurotrip….

I am traveling alone on the first leg of my trip, and then meeting a friend in frieburg Germany and we will be traveling together from then on. The planner messed up some of the nights so the days are not accurate prior to the flight into Frankfurt.