I had that concern when I did my BBG a few years ago. I planned my route as a double out-and-back. I'll explain a little further.
Since I live in the quad cities in IA (point A), I found that a round trip to Mitchell, SD (point B) and back gave me a SaddleSore route. I then found a route with a turnaround about 250 miles out, in my case, Crawfordsville, IN (point C). So after returning from SD, I could bail at home and still net a SS1K, or (as I did) continue with my plan and bag my BBG1500. So my route went like this: Point A - Point B - Point A - Point C - Point A. I didn't really stop back at the house in the middle, but when I went by, the sun was still up and I knew that I was in good shape. It was quite the security blanket, and I didn't have to spend money on a hotel.