Roadtrips in an EV still requires more planning than an ICE/PHEV....supercharger or no supercharger. The one trip over 200 miles one way I make a year I'll take the no compromise ICE/PHEV.
Whether planning is involved is largely dependent on the range of the EV, and the charging network.
The LR version of the three gives you 300+ miles of range, and worst case you're talking 200 miles of real useable range. So any trip under 100 miles one way you can do without worrying about charging at all. So that's really zero planning.
If a trip is over 100 miles then there just needs to be a supercharger, and again in most cases it requires zero real planning. I don't really do any planning at all when I get into my Model S to go to Portland. I wouldn't do any planning for anything along the I5 corridor or along the coast.
So when do I take the ICE vehicle? A vehicle that doesn't have adaptive cruise control, and is less of a highway car than the Tesla. So it means I'm not going to take it unless I have to.
In WA state there are still parts of the state that don't have a convenient Supercharger on the way to. I'm not counting other chargers as those would require more planning (destination chargers, public chargers, etc). The goal is zero effort.
When I need an actual SUV. Tesla doesn't make a real SUV.
When I need flexibility. The Tesla is awesome for fixed determined trips, but when you might end up anywhere than the ICE is a better option.
When it was all said and done I didn't really drive my ICE vehicle that much. So I ended up ordering a 4x4 Sprinter van converted into an RV.
So I went even further into the polar opposite between my EV, and my ICE. To afford it I need to downgrade in cost from the S to the 3. But, the 3 has more range and further reduces the need for an ICE.