Thats a brutal route. Cabbage and Snoqualmie. Cabbage can get a lot of frozen rain and ice, Snoqualmie gets what we call "Cascade Concrete" wet heavy snow with a lot of moisture content.
I did a dedicated for my company for a couple months, up and back Eisenhower and vail pass as well as Cheyenne to Pueblo. I couldn't get out of it quick enough. I couldn't get the company to pay added ancillary items and was getting milage pay on it, so it wasn't financially good for me. Aside from that sitting in Denver front range traffic all day was untenable. I couldn't imagine doing it in a day cab.
A tractor which does not have a sleeper berth attached to it. Normally used for local routes where drivers go home every night.
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I agree with these answers. Just clarify with your boss that if there are chains in your near future, you are authorized to pull to a motel for the night. And the company pays the hotel and meals for the weather stop. Your hours would match the driver log, so there should be little concern for your paycheck there.
Now another thing: Twice a week trips is not "every day", so take a break from tossing kegs and enjoy the season changes on the trip. And... in the long run of things, how often would I-90 close down? With the weather forecast you should know ahead of time. Plus, no delivery deadline takes priority over you or your truck's safety.
TWIC:
Transportation Worker Identification Credential
Truck drivers who regularly pick up from or deliver to the shipping ports will often be required to carry a TWIC card.
Your TWIC is a tamper-resistant biometric card which acts as both your identification in secure areas, as well as an indicator of you having passed the necessary security clearance. TWIC cards are valid for five years. The issuance of TWIC cards is overseen by the Transportation Security Administration and the Department of Homeland Security.