There's a couple things that make trucks a hard nut to crack(again I say this as a Model S + diesel truck owner).
1. There's a 6k GVWR weight limit for a lot of local streets. Most half-ton trucks are in the 5200k range so adding 2k of batteries easily puts you over this.
2. Trucks are rated for total tow capacity, adding 2k of batteries means you cut towing capacity by 2k or upgrade the brakes/drivetrain which adds more weight.
3. Trucks aren't that aerodynamic, trailers even less so. That means per-kW you're going to get a lot less range than something that has a good Cd.
4. Charging stations just aren't setup for trailers at all. You'd have to find a place to unhitch, charge and rehitch which adds even more travel time.
For commercial trucking routes you can probably go electric sooner since they are regular routes but for consumer trucks I don't see it happening soon.
Recently we had to drive 400mi roundtrip towing a 5k lb trailer @ 18 MPG. Going from a GGE of 37kw/gal * 0.5 thermal we would have needed a 412kWh battery pack to make that trip with 0% range left.