I can help with 1 & 2. My Compass is Sport trim with uconnect 5.0.
1. Standard Halogens, I'd grade like this: Low beam-B+, High beam-A+. The high beams are very bright and WIDE. I think HID's are available in Latitude trim.
2. The transmission is crazy smooth. I love it. It seems to actually "pull" itself into gear for you. The engine has enough low-end that it's pretty hard to stall out. And starting on hills isn't a problem with the hill assist. If you drive in mountains, you'll find that 6th is a little too tall, and you'll spend most of your time in 4th and 5th.
Hope that helps!