Time to DLR depends on which hotel you are traveling from and the route you are on. Best idea is to ask the desk staff at the hotel. They may have an idea based on past guest experiences.
We always just walk and have never done the route from the HoJo. It takes our family of 5 (or 6 if gramma is with us), about 8 minutes from Bldg. 2 to the Esplanade. If it says there are 4 stops, then yes, that's how many it should make.
I remember reading at one point that the HoJo was first on pick up route and first drop off on the return trip. Not sure if that is still the case.