Really want to jump on this but requires a reposition flight from NYC to SJC. that would be a long weekend of travel (Friday afternoon through Sunday Noon) including 2 red eyes.
Very similiar to the JFK>SAN>ATL>ICT>ATL>SAN>ATL>LGA MR I did last September. That was exhausting!
Reposition flight from NYC>SJC is not MR material ($420) range so the timing works out. Not sure if it's worth the miles though NYC>SJC>NYC is currently available on some days at 25k level for economy.