Yes, you will make it, you will just need to hit every one. But if you plan on doing many road trips buying the SR probably isn't the smart way to go.Honestly, "tricky" is even a strong word. I can guarantee you that on the super charger network, if you charge to 90% SOC in the Model 3 SR, you'll be able to make it to the next SC driving the speed limit, even in -40 weather, without worry for at least the first million kilometers of its life.
It would be nice to see the stock battery gauge factor predict things better. On my first cold road trip (well first road trip overall) it was snowing and 15 degrees and I had to majorly adjust my charging plan because I was losing 1.5 to 1.75 miles on the battery indicator for each mile I drove.
Now, that's partly user error I (and I assume most others) don't watch the gauge in normal driving. If I had watched that normally I'd have already expected to lose 1.25 miles (made up number) and then wouldn't have been so shocked by losing 1.75.
It's going to take some time for all of us to reorient our heads around the EV driving compared to ICE.