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Lindsey,
I'm so glad that you got up the nerve to ask for a raise. Congratulations! That's not an easy thing to do.
I'm the type to do one thing at a time, so I would discuss the raise at the first meeting with my boss. Then, once I felt that we had a good working relationship, I'd request a second meeting and discuss the other issues.
Bringing a negative (your supervisor, etc.) into a positive meeting - and he certainly sounds positive about you - offsets the energy.
JMO and best of luck. Keep us posted.
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