My son is at the school currently. I am not sure what ethical gaps there are with the current Head. People do talk a lot of nonsense on these threads. You'll find the people who are most vocal and critical are not representative of the vast majority of the parents and/or pupils views.
Pastoral care is actually pretty good now. The Housemaster is proactive and supportive, the school also has a large team of counsellors to help kids who need it.
Intellectually the school is very strong. The focus of the school isn't just getting the best grades/being top of the league table, although it is very strong on grades as well. A quarter of their time at A-level is spent studying a non examined subject designed to broaden their education and minds. It is excellent. They also spend a lot of time in class going beyond the syllabus. As pupils are mostly pretty smart and the syllabuses are narrow this offers a much deeper and wider learning experience of a subject.
Winchester is a very unique school, there is nowhere else like it in the UK. The best way to decide if it is right for you is did you and child like the people you met and the atmosphere, were you inspired? If so I'd go for it.
Generally Winchester is a lot kindler and gentler than most boys boarding schools. There is hardly any bullying and there is little jock sports culture culture. pupils are celebrated for being brilliant at the piano ass much as they with a ball and a bat. People genuinely respect each other for their intellectual and cultural achievement. That is very rare in a boys school.
In terms of drinking and drugs, yes I am sure it goes on, there is probably less of it than at most private schools. The boys are kept very busy, so have little time for that.
The genuine test when I look at my son and his friends is are the school making them better people as characters in terms of human decency and intellect. I'd in most cases the answer is yes.