TexTAC,
A temporary cable routing I have used a few times...
At the big-box hardware store get a length of AC/Water pipe insulating foam tube. About 2 inches in diameter and 1/2 inch wall thickness. Get the type without the sticky tape on the edge that holds it closed. Roll the window down on your vehicle about 3 inches. Cut the tube to length and tapper the ends to fit the window guide angle front and back. Lay on top of the window and press it down. Where you want the cable to pass over the top of the window, cut a 45 degree slit in the foam, but only thru to the bottom of the foam thickness and angled back so wind pressure will not drive water up the cable inside the cabin. Roll the window up, but not all the way, just enough to seal the foam against the top of the window slot. Water stays out, AC stays in and wind noise greatly reduced and cable not crushed. Very temporary setup best for rental cars or road trips in vehicles not your own.
Good starter radio I have recommended in many of the ham classes I have helped with.
Mike