Hey Guys

I'm new to mileage running and I thought I'd kick the new year off by trying to get EXP by the end of January by doing 9 round trip SFO-ORD flights. Since there will be TEQM, it comes out to 11184 EQM. I've scheduled some back to back flights with around 1 hr layovers in between. So SFO-ORD-SFO-ORD-SFO-ORD-SFO and since it's the middle of winter in Chicago, I'm a bit worried about the weather.

1. If the first flight gets delayed, that will potentially cause a ripple effect to all the other flights. If this does happen, can I rebook the last SFO-ORD-SFO to another day? Or does it have to be completed ASAP?
2. I've heard from people that 1hr layovers is a bit crazy, how much time would you allow especially considering the weather?

Thanks!