1) ORD as a new hire is a pretty good bet.
2) If you are willing to consider MKE as "North ORD" (which isn't really a stretch as I'm pretty sure that MKE is actually closer to 27R at ORD than the terminal is), then you effectively have a 100% chance.
3) No. we are not upgrading people early with if they have prior 121 time at this point.
4) 1-3 months depending on how long your training footprint ends up being.