Thinking of getting the S2 which is totally covered by insurance and also purchasing the S9 for the portability or should I just do the S1?

It'll come out to about the same out of pocket price.

I'm a standard 8-5 working momma with an hour commute, so I will be pumping 5 days a week, several times a day.

UPDATE: went with the S2. I could have paid 95$ for the S1 upgrade but since I'll be pumping in the car or in my office which has outlets, and just breastfeeding at home, I figured I'd save the 95$ and then just spend on an S9 or other portable pump or a battery pack or something if it turns out I need another option.