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taking cold into account when planning trip

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You seem to be saying two directly conflicting statements back-to-back, so I'm confused at what you're trying to say here. First, you say you're questioning my conclusion of more but shorter stops.
But then you "support" your disagreement by pointing out that charging at the bottom of the battery pack is faster than charging at the top. However, that is exactly the point I was making. The onboard trip planner very frequently has you charging up well over 90% and for 50+ minutes, well into that slow, tapering point of the battery pack, which is quite a time waster.
I see. So you’re assuming more frequent stops with shallower charges. OK. There are at least two more elements in the overall trip time computation (and like I said, I’m not going to try to recapitulate all the figuring that’s been done elsewhere, I’m just pointing out that these are factors):
  1. Driving speed. If you can skip a charging stop by driving at, say, 65 instead of 80, you might be better off doing it. (Simple example, an 80 mile leg. You can drive it in an hour at 80, or 1:14 at 65. If the extra charge time takes more than 14 minutes (including onramps and offramps, etc) you lose.
  2. Overhead — those onramps, offramps, feeder roads, Supercharger not directly by the highway, local traffic, stoplights, etc. All of that eats into your trip time without contributing anything positive.
All of which goes to say, “it’s complicated”. I doubt the nav system is taking every possible nuance into consideration, but quite possibly, some.
But yes, there is a human factor to "feels better", too. The tendency toward people feeling bored is not linear with time. People can find a few things to do easily for 10-15 minutes without really noticing, so with shorter stops, you can almost always avoid that annoyed feeling like you're having to wait for the car. But with 50 or 60 minutes of charging time, it's highly likely to achieve boredom.
And on this we agree. I just think the nav system may not be as stupid as you do.

Edited to add: I think the cognitive dissonance in my earlier reply came because I assumed you’d be driving in the top of the pack, charging to 80% or whatever. If you really do manage things to drive in the bottom of the pack, then yeah, you can charge much faster. I don’t like doing that because I like seeing a large range reported when I start out from my charging stop, and I don’t love arriving at the Supercharger with < 10% in the pack. More “feels better”, I don’t claim it’s completely rational.
 
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I think in general driving speeds around 80-90 MPH are optimum for maximizing travel speed. Any common highway maximum speed is likely not far off. Similarly, the trip optimizing apps are taking into account the extra travel to and from each Supercharger, plus usually 5 minutes of getting ready/finishing up time (one planner I use includes it in drive time, one in charge time). So I think the trip optimizers are considering pretty much everything they can and are likely finding the minimum total trip time strategy.

That said, I bet there's just a small few minutes between the car's long-segment plans and the super optimized trip planner plans. I've found I can add an extra Supercharger stop in a trip planner and lose a couple minutes or less in total trip time.

As long as you're following one of the plans you're probably not far off the optimum timing. The big problem is if someone stops at all the SC's and fills to 100%, kind of like an ICE car.
 
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I see. So you’re assuming more frequent stops with shallower charges. OK. (...) I think the cognitive dissonance in my earlier reply came because I assumed you’d be driving in the top of the pack, charging to 80% or whatever. If you really do manage things to drive in the bottom of the pack, then yeah, you can charge much faster.
Right, definitely doing the bottom of the pack. I am usually able to arrive with around 10% to 15% and then get that super fast charging up to 60 or 70% and go.

Driving speed. If you can skip a charging stop by driving at, say, 65 instead of 80, you might be better off doing it. (Simple example, an 80 mile leg. You can drive it in an hour at 80, or 1:14 at 65. If the extra charge time takes more than 14 minutes (including onramps and offramps, etc) you lose.
This is something that is very dependent on georgraphic region as far as cities, traffic, etc. Where I am, out in the sparse Mountain West, like Idaho, Utah, Nevada, there are two factors: 1--there are so few Superchargers that they are usually at least 120-150 miles apart, and it isn't usually an option to skip any. 2--Smaller cities with less population means small area and very little traffic, and it's usually 5-ish or less than 10 minutes to go from highway to Supercharger plug-in, so it's not usually much delay.

The big problem is if someone stops at all the SC's and fills to 100%, kind of like an ICE car.

In my first few years, I met someone at a Supercharger who was borrowing a Model S for a business trip because it was one of their company cars, and she was pretty stressed with not knowing how to tell if she had enough, so she was filling most of the way up at every stop--very inconvenient. I showed her the trick for setting the next Supercharger in navigation and then being able to leave when your arrival % showed some comfortable margin, like 15 or 20%. Then, you don't have to go way up into that slow tapering of the charge. This was before the trip planner, so the car didn't give any "ready to go" announcement.
 
Short trips make cold weather energy use look HORRIBLE battery and cabin warming swilling juice, that tapers and plateaus on longer trips.
Keep this in mind for starting out cold in mornings, initial energy use will be high and this might lead to needing an extra stop but if you can wait it out you might find use taper down enough that you will make the next stop.
My first cold weather trip the car was not sufficiently preheated and car warned me to reroute or slow way down to make destination, I rerouted but then energy use began to fall and in hindsight I did not have to reroute. While it does not account for weather it does look at your current use trend and recalculates on the fly. It will prompt you to reroute or slow down if the next stop is in jeopardy.

Also be aware supercharging cold does not work well, battery has to warm before rate ramps up, so if you have to do so give it a generous preheat or drive before going to the supercharger.
 
Stopping after every 30% is probably good for minimising depth of discharge (about 100 miles on the long range battery depending on speed) if you plan to keep the car for as long as possible, so it would be good to be able to see all on the map
 
It is an easy matter to see all the superchargers on the route, by clicking the "superchargers" button on the map. Then you can easily navigate to the supercharger of your choice. I found it made sense to be aware of all the superchargers, and stop or skip as we "felt."

I have done this trip may times in ICE vehicles, often burning waste veggie oil, and one of the main differences is making more frequent stops in the Tesla. It did take longer for us. Not necessarily worse, but different. Definitely more coffee. I will look forward to even faster superchargers, which will help a lot, but I also think that 310 mile nominal range isn't quite enough to put EVs on par with ICE vehicles for long trips after you figure in reduced range due to cold, rain, and windshield defogging (for which you often frankly do need heat), and that it feels like a big waste of time to charge over 80% as the charge rate slows so much. I'd not be surprised if Tesla starts producing an "extra long range" option on Model 3 in the near future, maybe 400 miles, to really put the "hard smackdown" on ICE.
 
It is an easy matter to see all the superchargers on the route, by clicking the "superchargers" button on the map. Then you can easily navigate to the supercharger of your choice. I found it made sense to be aware of all the superchargers, and stop or skip as we "felt."

I have done this trip may times in ICE vehicles, often burning waste veggie oil, and one of the main differences is making more frequent stops in the Tesla. It did take longer for us. Not necessarily worse, but different. Definitely more coffee. I will look forward to even faster superchargers, which will help a lot, but I also think that 310 mile nominal range isn't quite enough to put EVs on par with ICE vehicles for long trips after you figure in reduced range due to cold, rain, and windshield defogging (for which you often frankly do need heat), and that it feels like a big waste of time to charge over 80% as the charge rate slows so much. I'd not be surprised if Tesla starts producing an "extra long range" option on Model 3 in the near future, maybe 400 miles, to really put the "hard smackdown" on ICE.
I'd be really surprised if the 3 gets a 400+ mile option before the X or S do. I predict we will see an X and S refresh in the next year or so with 400+ mile option and ability to use Supercharger 3.0.