There are different types of expensive boarding schools for different students with different reasons to attend a boarding school. I attended an elite, academic boarding school. There were HG+ and PG kids that made it all seem so easy and kids subsequently went to elite universities, where it was easy for them, too. Not that they didn't have to do work, too. There is a certain amount of knowledge and production that must be obtained and completed in order to achieve and matriculate into elite universities. The top, academic boarding schools have significant financial aid packages and have easy-to-use financial aid estimators on their websites. At Exeter, it's free for those making $75,000 or less and families making under $200,000 qualifies for financial assistance. So, I wouldn't be overly constrained by finances nor would I be overly constrained about whether top boarding schools have enough HG and PG kids. They do. I would worry about whether your 14 year old kid can emotionally handle living away from home in an environment where they will not longer be the brightest fish in the sea. I saw lots of kids, particularly the 13 and 14 year olds, that just couldn't hack it.