I think you'd be fine if you charge to near full in Estevan and at least start off driving slowly. You can walk through the "mall" to get to the Timmy's and wait there for a while if you like. But obviously you'd want to check the weather, especially looking out for a headwind.
All that being said, Google Maps says it's 6 minutes faster to go through the Hat and Milk River than it is to go through Estevan and Glendive. And that would definitely be an easier route charging wise. If you want to make a loop out of it and take one route one way and the other route the other, it would make more sense to return to Regina through Estevan as you are more likely to have the wind at your back in that direction (also Estevan is very slightly lower elevation than Glendive which is a small consideration).
EDIT: It looks like Helena to West Yellowstone is also a problematic leg if you take the direct route (lots of elevation gain), so maybe the route through Milk River could be a few minutes "slower" since you would probably want to make the diversion to the Big Sky supercharger. That being said, you will save more time than that by not having to charge to full in Estevan and not having to drive slowly from Estevan to Glendive.
I never drove that route myself, but @Bighorn did drive from Regina to Glendive back before the Estevan supercharger was open. He plugged in at the Peavey Mart in Weyburn and took a nap there while he charged for a couple hours. I think he also had backup charging options in the Williston area, but I can't remember if he actually used them.
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