1. Check out the thread on Silver getting E+ at OLCI. Pretty good news. As a Premier Gold, I've never not gotten an aisle/window in the exit row/bulkhead.

2. Not very good odds, leaving from ORD. But it does happen.

3. No. Just walk in, get the application, and apply. Cancel your PP soon after.

4. Where you have the time, book one-stops or more, instead of direct flights.