I don't think it's possible, but at 40K for 8x500 miles it doesn't seem to be worth it. You can upgrade each way for 15K miles (compared to 5 500-milers for a transcon) or get CR1s in the coupon connection. If you want to upgrade lots of short hops the 500 milers may be more convenient, but who needs to upgrade on short hops anyway?

On edit: I see you're a 1K so you should have upgrade instruments to boot. . Why do you want even more?