what everyone here is missing is that the OGG-OAK flight arrives in OAK at midnight. the train is just not an option for same night travel at that point. even renting a car in Oakland will take 40 minutes since all the car rentals are at a remote site. however, AS will cover the car in this scenario IME, if the OP presses them to do so and gets the record annotated as such. the voucher would be issued on arrival by an AS agent in OAK.

i wouldn't drive to SFO for the VX flight, but that's just me...for several reasons: (1) the traffic to/from SFO is monumentally worse than one way from OAK (2) the outbound flight arrives in Maui at 9pm versus the noon arrival from SMF (3) the return flight is a redeye versus late afternoon departure from OGG to OAK or a late morning departure from OGG to SMF.

the OGG-SMF flight is sold out in F from 5/17-21 and 23, 24 so we must assume OP is traveling around that time period. on those dates there are non-redeye options on HA, DL, and/or UA every day for under $1000. if it were me and I already paid the going rate for AS nonstop F which is usually around $800 one way, I'd take the refund and buy something else.