Colorado Continental Divide for the first time?

Depends on when you would be planning on returning. Be situation aware. If the weather looks like it won't cooperate, return via the southern route. Towing where there is snow is bad enough, but you don't want to encounter ice. We used to tow with a Ford Escape with 3500 lb. rating. We encountered ice with a strong cross-wind. We now tow with a Frontier with 6100 lb. rating. Our 179 also had to go to the factory for extensive repairs.

Remember that you are towing a big sail. It isn't just the snow and/or ice. It is the wind that can push your TV and trailer in ways you don't anticipate. It is much better to wait until you can be relatively sure of not encountering snow and/or ice on the trip.

To help avoid the same situation, I added a Hayes Sway-Master electronic sway control. It should help if we should ever encounter a similar situation but the best way to avoid problems is to anticipate and avoid risky situations if possible.

You don't need to go over Loveland Pass.  I-70 actually goes UNDER it,  via the Eisenhower tunnel.  Vail pass is fairly steep  ~8% in some spots, but it is still a four lane highway with slow moving traffic lane.   Trying to miss the snow is the key.  

Stay south until April