This was the first time I had as well and yes, it went very smoothly. I'm at Riverside not CS, but again, Disney didn't have Riverside at the discounted price and Expedia did

I had to pay upfront, but I would have had to with Disney as well booking last minute.
Nico is 14, so when I told him I was buying him a tux, he didn't tell me no.

WE just went through the Navigator because in the latest one I could find, Aladdin (which is the formal night show) was showing 3 times. I told my kids we are getting a formal picture together, so we needed to kind of go through and plan when to meet up for formal night. I either wear jeans with a body suit or a long skirt. Probably changes depending on the weather, but I am always cold. I know body suits are so out of fashion, but I don't care. I hate shopping that much.
I don't remember seeing on the Navigators any tickets needed for Disney Jr, but my kids aren't into that anymore, so I'm not sure I would have paid attention to it. When they hand you the navigator after checking in, read the very front page and it will tell you where and when to pick up Anna and Elsa tickets. It is usually as soon as you board, but the location has been changing. If you need to pick up tickets for the Disney Jr characters, I imagine it would tell you on the Navigator as well, but you can always ask when you walk in to make sure.