I try very hard to get out 2-3 times a month and I plan for 2 week long trips to a good dark sky site. Here in Ky the skies are usually pretty thick in the summer months so,I try to get to The WV mountains when possible. I try to make my week long trips in the spring and fall months when the chance for clear dry air is the best. I would observe more if circumstances would allow it.
Like Preston, just once a month under dark skies. And one other session for a couple hours under the bright skies of LA for the Moon and planets.
I have averaged 10 dark sky sessions per year for the last 8 years. That's why I always try to observe dusk to dawn when I go out. It's too few
hours under the stars otherwise.