My observing habits have changed drastically as a result of aging. As a cautionary tale, understand that many things you take for granted today will degrade, or disappear altogether. Remaining engaged becomes a matter of working around these losses. Not surprisingly, the most discouraging is steady loss is visual acuity. This starts in one's 40s as the inconvenience of presbyopia makes it a challenge to switch between near a far. I remember first working around this by using magnifying glasses to read things in the dim red light. Count on needing separate reading glasses and star hopping slowing down considerably as you move between looking at charts and at the skies.
In fact, thank heavens for digital setting circles! Not as a crutch for laziness, but as a critical tool to simply locate objects—especially the tough ones in those relatively blank areas of the sky. I did my time star hopping, a skill I was proud of, so I feel only a little shame in turning to them out of necessity. Floaters and the early stages of cataracts makes it impossible to even see the less bright stars. Finding the Sombrero Galaxy, something I could quickly point to in past years, would be an exercise in extreme patience. Indeed, hallelujah for 10K encoders! Also, you learn to hang on to anything else that helps: more aperture, better eyepieces, and don't forget the observing hood!
Age improves the vintage of the best and brightest objects, and heightens the accomplishment of tracking down the really obscure ones. I look at fewer objects in an evening, and I enjoy them more. There really is no limit in how many times I can look at, say, M104. Seeing it many times over the years through different combinations of optics and under different viewing conditions gives perspective. Every once in a while I see an object better than I can remember ever seeing it before: that is a grand moment. Getting a glimpse of one obscure Hickson group can give meaning the the entire session. A really good night is a combination of old favorites and fresh challenges.
I used to jealously guard observing time for myself. Sharing the eyepiece with others only slowed me down. Now I find sharing improves my odds of tracking down the challenges. Setting aside a little time sharing with newbies is almost a duty, one that occasionally allows me to re-exerience some of the early wonder I remember. Observing has become more of a social experience. I'm more interested in quality over quantity. If I can go to bed with one really good obscure faint fuzzy, I'm a happy observer.
One big advantage of being a "seasoned" observer is that we generally know what to look for and how to look for (or at) it. Our visual acuity may be shot to hell, but we are now cunning. And patient! Despite the challenges, I think I'm a better observer and definitely one who appreciates the moments better.
Kemer