Switching over to a heat pump system with the Model Y introduction really helped Tesla's cold weather performance. Preconditioning before driving helps too. The real world range is still different, but at least it's relatively grounded in reality.
250 mi with those requirements is still a stretch by a little bit. One will see a pretty solid hit going 70+ mph and winter tires can reduce efficiency. Dropping to an 18" rim makes it a negligible difference from what I hear though. Add in a just-in-case buffer (20%) and I'd be comfortable predicting 180±20 mi from 100%. That's about 2.7mi/Kwh for reference.
Personally I have no interest in driving 3-4 hrs without stretching my legs so I'd take 15 at a convenient fast charger along the way and add an extra 70-100 miles of winter range while doing so.
Ultimately I haven't found using a BEV as a road trip vehicle that limiting, though everyone's use case is different, it just requires a little more forethought in really remote areas.
What I do find limiting is ground clearance, since there really aren't any reasonably priced high-range BEVs with north of 7-8" down the center line sans modifications. Keeping my fingers crossed that Rivian changes that with the R2 and R3x.
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