You didn't mention what your elevation is, what direction the hill behind you is, how wide the hill is ( the width of the arc it migh block signals from). If you can put the tower(s) near your house and the hill only blocks to 8-10 degrees, so that your line of site to the horizon is at least 10 degress, or if the hill blocks higher than 10 degrees, but there aren't any worth while, or hard to get countries behind the hill, closer might be better than stringing 600-900 feet of AC. For me, in tucson AZ, I don't worry about any hill blockage due south, the first country due south of me is long path to India, which typically is a little skewed to the west, and not due south. Some hams I've talked to have remarked that when a band starts to open, low angle beams work best. But as the signals get stronger, the signals arrive from higher angles.
Have FUN
Bob