Winter tires are a real question here
All-season tires are a compromise that works in mild winters and struggles in severe ones, because the rubber compound hardens as the temperature drops. Montana winters are the case the compromise was not designed for.
A winter set is a different class of tire rather than a marginal upgrade, and whether you need one depends on how much you drive in it and where. Ask the store what people in this area actually run; it is a more useful answer than a general rule.
For a fleet, the winter questions are pressure and alignment rather than tread pattern. Cold air lowers pressure, an under-inflated tire runs hot and wears badly, and a unit out of alignment on an icy road is working against itself.

