Lots of great points. Already mentioned are:
1) Distance off route to Supercharger
2) Charging at the lowest SOC% is much faster than otherwise
Not mentioned:
3) Familiarity - time spent driving around looking for the charger (some people enjoy the challenge, but it can eat time) will definitely kill optimum overall travel time. If you're familiar with the site, this doesn't apply.
4) Weather - It's easy for even experts to misjudge power usage in windy / cold / rain / snow conditions, therefore novices will need a bigger buffer than experts. If weather is a factor, hedge your bets and "tanker" electrons. Don't plan to burn down to 10% on every leg, even though that will afford the fastest charge rates.
5) Busy chargers - this goes to familiarity a bit, but if you show up at a charger with every "A" side busy, that leaves you with a half speed "B" side. In other words, even a 4 stall Supercharger is "busy" with potentially just two cars. Skipping a charger to arrive at one with half speed didn't save you any time.
6) Holiday weekends - Friday / Sunday nights, and particularly holiday weekends are almost guaranteed to be busy anywhere near a large urban area, but even Bozeman, Montana can suffer this fate! Again, busy chargers equal slow chargers (or worse, waiting).
7) Detours - Do you really know where all the detours are prior to launching? Dropping to 10% or less on every leg to optimize charge speed can really backfire with a reroute and you gasping for electrons. I'd recommend spending at least a little quality time while charging to ensure that the road is at least forecast clear for the next leg. Obviously, the overturned truck / train derailment / major accident / incident can't be planned for.
8) Plan B - For those unplanned issues, plan for an alternative. For something bad enough, that means a whole lot of Tesla cars might all be competing for limited alternate resources, meaning that the best prepared will find those RV parks, hidden J1772, or CHAdeMO stations first.
9) Regional power outage - This is tough, because skipping a charger means everything must work at the next one. Rural areas in bad weather are far more likely to experience an outage than a major metro area. But, without power, no easy charging options exist, and if you burned down to 10%, you can't make it to the next one.
In a nutshell, there is no perfect right answer, because some things are out of your control. Only your degree of risk will determine how you handle skipping charge stations to burn down to low SOC%.