Aspen vs. Telluride
That's like asking me which one of my children I love more. Both of these places are very special to me and offer magical settings for a ski vacation you will never forget. Having said that, here are a few of my thoughts if a choice was to be made on which of these spots is better suited to your wish list.
First of all, you should know that both Aspen and Telluride are pricey. So I am assuming that you are willing to give up a few extra nickels for breathtaking scenery, outstanding terrain, and no lift lines. However, if you are on a tight budget, you may need to look elsewhere since it is very difficult to find bargain deals at these spots.
I'm not going to spend any time distinguishing the two in the areas where they are virtually equal or close in comparison. I will focus on those areas where I think one spot clearly has an advantage over the other.
Beginner Terrain: Telluride. Without a doubt, Telluride is one of the best places ANYWHERE to learn to ski or to improve on your budding skills as it has what I consider to be the best beginner terrain in the Lift 10 area (a/k/a Sunshine Express) and gives beginners the ability to ski on runs with almost 3,000 vertical feet (Galloping Goose).
Intermediate Terrain: Aspen. Telluride has decent intermediate terrain, but Aspen has about 100x more of it at all four of the Aspen mountains (Aspen, Snowmass, Aspen Highlands, and Buttermilk). Aspen is intermediate paradise.
Advanced Terrain: Aspen. This is a closer call as I love the front face of Telluride, but again...Aspen just has more. (And it also has fast lifts unlike Lift 9 at Telluride which seems to last forever.)
Expert Terrain: Telluride. Probably not pertinent to the OP, so I won't go into any more detail here.
Accessibility: Aspen. Just about every place in the world is easier to get to than Telluride.
Non-skier stuff: Aspen. Telluride has plenty of stuff to do for non-skiers, but again...Aspen just has more.
I consider everything else to be just about equal, including ski school should anyone want to take lessons.
I'm locked in at Aspen for January coming. If I had have known Mountain Collective was going to add Telluride I would be doing a back to back comparison. This way I'll go back next year and do Telluride. Your description sounds wonderful. Can't wait.