I am currently doing my CP in Transportation and I absolutely love it! I can't speak for all of the areas but the Friendship boats are a great place to be. The other options are Magic Kingdom watercraft, Monorails, and I think they just added Bus Greeter. The best part about the boats I think is just that we actually have to learn how to drive them and it is a real (but not necessarily useful, lol) skill and it is a real responsibility and sometimes a real challenge. I know it is hard to get Transportation because all the included departments are pretty small in comparison to attractions and merch and their are a lot fewer areas to choose from. For example, my department has 11 CP's right now and only 2 were added in August, the rest have been here either since January or May. I did have boating experience which I think helped me but most of the others don't.
I don't know how sought after it is though. From what I have noticed on these boards it seems like that role is added as an after thought for most but it really is a great place to be. I figured I was in the right place when I got to casting on the first day and a cast member there saw my role and told me how lucky I was to get it because most cast members have to build up seniority in other departments in order to transfer into those roles and CP's are some of the only cast members who get to start out there.
This is all just my experience so far but I hope it helps!
