Hitch, do you own the house or are you renting?
I had similar situation with a house I owned, the former owner had used rubber cement on most of the windows. What I did was this, I drilled a hole through the bottom of the window sill. Then I went to Lowes and bought one of those screw together coax entry tubes the cable guys use. I used some silicone to seal the flanges on the entry tube to the window. After I threaded the coax through and got the antenna up, I gave the tube a shot of expanding foam to seal it tight. It worked well.