Going into Pagosa Springs involves more than "crazy hills" no matter the direction. It is deep into the mountains. I would go north from Shiprock until you reach US160 and proceed east at Cortez through Mancos, Hesperus, Durango, Bayfield and Pagosa Springs. When you say "the Springs" in Colorado people think you are speaking of Colorado Springs.
If you are going to Alamosa the trip over Wolf Creek Pass from Pagosa is the best route. You have plenty of equipment. If you go south it is mountainous with lesser roads. By lesser roads I mean two narrow lanes of twisty roads to get across the San Juans of New Mexico crossing at Chama (2 passes Cumbres and La Manga) or Tierra Amarilla. Brazos Summit between Tierra Amarilla and Tres Piedras is 10,550' the second highest in New Mexico only 300 feet lesser than Wolf Creek Pass. Both NM routes entail passes which are no easier for you than Wolf Creek Pass. Take your time there will be many campers on the 160 route. They have plenty of lanes for slow traffic.
Enjoy the sheer beauty of Wolf Creek Pass and the Mighty San Juans!