Navigating at night is one of those things that gets easier the more you do it. Eventually you’ll feel as comfortable at night as you are in daylight, but it takes time. Just getting used to living with a headlamp takes some a number of nights to adjust to. When kids are old enough that they are ready to start learning more about staying out and route finding at night, there’s nothing better than picking some nice summer weather and just doing it. Approach it like it’s fun.
Same for adults, just do simple things in the dark and it takes all the mystery away. If you don’t have time after work for long hikes, maybe take one evening a week and do it half in the light and half in the dark. With our hiking club I used to organize a 4 hour round trip up a small peak every Wednesday so we’d be on top to see the sun set, then work down in the dark. A couple times a summer it can be fun to take a long hike or go backpacking at night. Peak bagging leaving the trailhead at midnight is one of the most unforgettable things a fella can do.
How viable bushwhacking is varies a lot depending on vegetation, topography and game trails. One area 5 miles from the trailhead has a big well defined set of game trails and easily identified openings to stay oriented and coming down hill is fast, super fast, like the fastest 5 miles you’ve ever hiked. Other areas have barely defined tiny game trails that always peter out, lots of blow down, patches of thick small trees that are horrible to work through, rocky knobs and projections you have to work around, big drop offs, avalanche chutes, or random super wet areas bordering the creek you have to cross. Rocky dry creek beds with big boulders may be passable, but just going up and down all week can be extra hard on the joints.