Questions about Day 1 -

What time do you arrive in Denver?
By the time you pick up the car and drive to Colo Springs, that is at least 3 hours.
Drive to Pikes Peak - and the drive to the top - what time will you leave for Pikes Peak - how much time have you allowed?
Very thin air at the top - you have not given yourself any time to adapt to the altitude. At 14,000 ft, unless you have some special preparation, you are likely to have trouble. I wouldn't want to be the driver.