I really, really hate to be a naysayer -- I am a great believer in adventure and taking moderate risks.
But.
Towing an old trailer on slippery winter roads as a newbie is not a moderate risk. Ironically, the biggest problem is the Caravan -- I have towed a small trailer with a Caravan, and the vehicle was not suited to long downgrades.
No matter how much I downshifted, the brakes would get hot. The rotors eventually warped.
Taking the van without the trailer would be a lot safer.
You'll have to run the numbers to see if driving is any cheaper than flying.
Good luck, and stay safe.
