Yes. there is a setting to force start / stop roles (so the timer does not stop when jumping on start a second time). There is also a setting for

Several hundreds, as much as the internal memory of the device allows.

It's possible, but I would recommend using jump wings. I haven't seen any course ending or starting in tunnels, not even hoopers or tunnel cups. But It can definitely be

The bean can be considered a line, you would have to move depending on size.