Hi Claire, I reviewed Fleche routes last year and will probably be the person reviewing Dart routes this time around. (Rob, I hereby volunteer for that role if you'll have me.)
What I'm looking for when I check a route is: are the controls placed such that the riders can't skip meaningful sections or features of the route? I don't expect riders to take the very shortest path from control to control, if there's another path between controls that is clearly preferable in practice (be that because it's safer, more scenic, fewer turns, less climbing, etc). But I do want to make sure that the controls enforce the general concept of the route.
Taking the Berkeley/Oakland Hills as an example, if your route started at the bottom of Wildcat Canyon, went over Grizzly Peak, then took Skyline and Pinehurst to the Pinehurst/Canyon intersection, I would want controls not only at Wildcat Canyon/SPDR and Pinehurst/Canyon, but also at the top of Grizzly Peak, or maybe better, at Wildcat Canyon/South Park. Without that middle control, you could just stay east of the hills and skip the "general concept" of climbing to the ridgeline.
To make sure the controls are sufficient, I usually use the Strava route planner, set to "follow most direct," and see how much shorter/easier the resulting route is compared to the designed route. I'm not militant about this - if the shortest path between your controls is a bit short of the target distance, that's OK by me. (Especially because almost everybody submits a GPS recording as their proof of passage!) But if you come up way short on distance, and whole meaningful chunks of your route could be bypassed, I'll probably ask you to add a photo control or two. I try to make these fun/recognizable selfie spots so as to enhance, rather than dampen, the fun of the ride.
All of which is to say, don't overthink it. Focus on designing a route that you'll enjoy riding, and then we can work together to ensure that the bigwigs and sachems back in old France will be satisfied you really did it, hopefully without overburdening you with administration along the ride. But, you know, randonneuring IS "cycling with paperwork," so perhaps it's best to just embrace that ;)
I hope this helps! Glad to discuss further.
- Drew