How much initial timing is too much? Running hot on the highway.

That shroud surely hinders airflow at higher speeds, but removing it will no doubt cause hot issues at idle and cruise speeds imo.
I would look into fabbing some one-way flaps in the shroud which open up when the airflow into the shroud demands it.

this seems like a great idea. cut pieces out of the biggest areas in the shroud and install a small hinge or two on the top of the pieces so the swing open at speed.