OK, here are my thoughts - having lived in CO and been to many places you mention.
I would make reservations and start looking now. Will be busy.
CO Springs. Cheyenne Mtn SP is the place to stay. In that you have a toad you will want to drive up to top of Pikes Peak. Also see Garden of the Gods.
Route 50 will be fine. Some grades, of course; you are in the mountains. :-)
Not much in Gunnison itself and don't know where to stay as never stayed there. So west to Black Canyon of the Gunnison. Can stay - as we do - at the KOA in Montrose.
Also rather than Gunnison go up to Buena Vista. Great area. Get to St. Elmo.
Enjoy - great area.