Quandary would also be a good one to consider. You could stay in Breckenridge before and or after the climb. You can also get to the TH (like Yale) with a passenger car easily with a very short section of gravel road.
Your profile says you are from Florida. One thing that takes a lot of in-shape people by surprise is how hard the elevation gain is at higher elevations. I climbed Sherman with several people who are in pretty good shape. It's only a little over 2000 ft gain, but half the group decided that the saddle was high enough for them. But then again, two of us decided to go for Sheridan, also, while we were there. As I remember, Sherman has a wee bit of exposure on the ridge, just before the false summit. But awesome views of Elbert, Massive, and a lot of the Sawatch range.
If you're near the San Juans and preferably the Lake City side, depending on your vehicle, Handies is scenic and a walk-up with no exposure to speak of. Good wildflowers, and a neat mountain lake, and less than 3000 ft of gain via the American Basin route.
If you are in the Denver area a good warm up/intro to high altitude it mt sniktau. It is only 3 miles round trip and climbs to 13,400 ft. It has very easy access from Loveland pass as well. This hike will give your group a good idea of what its like to hike at higher elevations