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Need help getting upgrade on AA

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We have well over AA 250,000 FF miles. Due to medical problems we would prefer to fly business or first, SAN to JFK where we visit son. Not elite or platinum or whatever...just regular. Never have done this before..

1. How do I get upgrade?

2. Would I use miles or cash?

Our next flight would be BOS to SAN (we take a train from NY)..we love trains and it's easier for us than going to the airport.

3. would it make sense to fly back to JFK and make this round trip?
Only non stop from BOS to SAN is Jet Blue. No business or first. We got extra leg seats last time but it was not great.

Appreciate your help.

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