When he says "Lets see if you guys can do 90" and goes for 4th, he turns them on again, looks at the display and notes the dates are entered.
Nothing in the script indicates this, though it is not ruled out.
In the script it just says "Gauges and indicators light up behind Marty*s head, just as they did before Einstein traveled through time", not that he sees them. Watching the movie, it looks to me as if he keeps a close watch at the car's original speedometer and is oblivious to the time display or the extra speedometer fitted by Dr. Brown.
I agree that it looks as if he is driving straight at the toll booth, but he is also startled and blinded by the bright sparks and flashes, possibly causing him to lose control of his vehicle.
Since jumping through time does not require driving through an object, someone wanting to execute the jump but is not 100% sure it works would probably not aim deliberately for an object in case of failure. To me it looks like he was about to avoid the booth and hope that the following van did not have as good handling as a DeLorean.