I can navigate the night sky in the northern hemisphere fairly well. I learned in Boy Scouts and in the Astronomy Club when I was a kid. We learned some basic celestial navigation when I was in the Coast Guard too. I've been doing it for 30 years, so I feel comfortable with the exercise.
Often times, I will plan out my night... usually only an hour or so. I'll check out Stellarium on the computer, review my observation guides for the month, make some notes, grab my planisphere, and head out. If I'm using the refractor it's not that big a deal, but if I'm using the refractor or my big Dob, I've got to set those out earlier to get temperature acclimated. When I lived in Texas, California and Arizona it was no big deal, but these cold winter nights in NE Ohio are brutal and those, as any astronomer knows, are the best time for Northern Hemisphere viewing.
I'm considering getting a SkyShedPod or a NexDome for the back yard to help protect me from the elements and lengthen my viewing sessions. That is also why I'm considering the computerized assist... I can set up and get on target much quicker. For me, it's getting to be about practicality. I don't enjoy being out stargazing when I'm freezing my tuchus off. Plus, the kids don't come out in the wintertime, only the summer. I want to be more efficient when I go out.