I like TEX, ASE, EGE and SUN for the reward of the challenge. Besides, as a bonus you often get MTJ, GJT, RIL and TWF instead anyway! Wx can be the difference between an easy day and a real hassle. I live for windy days. If only the charter coordinators could be made to understand the logistics of mountain charters. As soon as you get one half trained, they quit for a higher paying job at Starbuck's. So nobody bothers.
Hate LAS and SFO for the delays. DTW for incomprehensible taxi instructions and routing. PHL for the rudest and least competent ATC. BOS for their ridiculous attempts to appear "security minded". ACK for the mile-long ramp full of jets served by a phone-booth-sized FBO. FLL customs. (enough said!) Did I mention I hate Vegas?
Though they have their challenges when the weather comes in, I respect what TEB and MDW ATC do and have not had any bad experiences there. Bring your "A" game though. And remember, wind is fun!
A couple of other airports deserving of mention are Tuckee-Tahoe (TRK) for it's mountain challenges and SMO for it's subtle but numerous headaches.
Favorite destination? Vancouver, BC. (CYVR) Love it!
Of course, your mileage may vary.
Best,
charter dog