SAVE YOUR MONEY AND GO TO MHSSC. Skiing with Shea Flynn, Maks Gorham, Nolan Willard, and Keiran McSlay for a week was insane, and I had literally no complaints about my week there. Except maybe that I wish I had gone earlier so I didn't have to hike the park, but it's not too bad.
Most of the people who go there are chill, and the counselor's are all great! I had a friend who went to Windell's for a week and he said that he felt as if he was too old for it at 16, it felt to "kiddy" for him. If you're 15 or older (I was 17 last summer), you stay in the coho cabin with all of the older guys, and it feels more independent.
So basically, if you're paying for most or all of your way to Mt. Hood like I did, save a good chunk of money and go to MHSSC, trust me, you won't regret it.
Of course, if you wanna go to Whistler in the summer I have no experience with that. I have some friends who dig there and they've been obsessed with it since they were 15. It is like a grand more than MHSSC though.