Let's assume a simplified model with lightning strikes at the T. Line close to the substation were two waves will splitting in opposite direction of the fault traveling at the speed of light.
a) Wave traveling away from the substation: Due to the smaller impedance, this portion of the current may be larger than the other one and successively drain most to ground in adjacent towers until the current decay. Smaller current may reflect but will also decay for losses and drained into the earth.
b) Wave toward the substation: This wave will reach the insulator and reflected almost duplicating the incoming crest value. If the peak value is greater than the insulator BIL, a flashover will occur draining a large portion of the current into the ground via the tower. Otherwise, the wave will be reflected back until finding a path to ground in the adjacent towers.
No, as described above, the reflecting traveling waves will be decay in a relatively short time frame. They may be a possibility that the system recloses if it is sensed as a ground fault and the line will be back in service to the normal operating state since a fault on a line has a self-restored characteristic. Worst case scenario, the protection system will trip the line permanently in the event of damage or large striking current.
It depends. We are assuming that somebody in the utility and the engineers of the line evaluated the pros and cons to operate the shield wire insulated (ungrounded) in the last structure. In most HV applications, there is a benefit for the protection system to have all the shield wires interconnected to the ground. Additional benefits for reducing the current injected into the ground by increasing the splitting factor of fault currents for grounding design in the substation.