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I've never had issues with driving. I've used bikeflights and have had a hanger bent on a steel bike--which Bike Flights compensated me for. I just don't like the headache of unpacking the bike as I'm a lousy mechanic and it seems things are never quite exactly right out of the box. (Wireless shifting would solve this). I, too, am curious about your route.

You can buy a cheap, $20 protective bike cover on Amazon. It will likely rip in the wind but it will still be worth it. My go-to for races in Arizona in the winter. By the way, I'd love to talk routes. I live in Boulder and have friends in Telluride and can potentially be a helpful resource. (I'm on the Divide though FYI)

If you decide to drive, you can also get a protective cover for the bike. I've seen them, but don't have any direct experience.

I have shipped a lot of bikes and often use BikeFlights or UPS. Fortunately, I haven't had any problems. As long as the bike is carefully packed, paying extra attention to the fork, derailleur, and wheels, you should be good-to-go. Insuring the bike for what it would cost to replace it provides an added sense of security. If you have a friend in Boulder who can receive the bike for you or can arrange for it to be held at a local UPS store, I'd have it scheduled for delivery a few days before you arrive, just in case there's some sort of delivery delay.

I'd much rather drive with my bike than fly with it. 10 times out of 10. I've never heard of wind-related bearing damage, but I suppose driving in constant heavy rain could be a reason to pull the bike inside the car. That said, in more than 35 years of cycling (and driving), I've never had a bearing failure related to transporting the bike. You should be good.