Hi FaF,
Any school will have pros and cons but I hope I can give you a balanced view after five years at Winchester College. At the end of our journey with so many ups and downs, our boy had an Oxbridge place so it worked out and a second leaves this year. I will happily tell you that we tutored them for the last three years as we didn't think he was being taught properly in his target A Level subjects. We did so in and around the sports timetable as they have a LOT of unsupervised time that they can use for online tutoring.
Pros
We love the diversity - pupils from all over the world, speaking many languages gives it a cosmopolitan feel. A strong bursary programme means there's lots of kids that our son wouldn't ordinarily encounter. Community Service is also amazing. At the same time,
It's not flashy or London centric and most are nice kids and parents
Throughout his time, he was free to be a "boys boy" and the (mainly) boys school environment has been great for him. In the Sixth Form there are something like 15 girls with aims to go fully co-educational from 13.
Lovely facilities as you'd expect for the price.
Winchester is really safe.
Cons
On the whole the last two years has been disappointing for us. Academic results and Oxbridge stats are poor for a school like Winchester. I can't tell you exactly why but most of his friends missed out on their Oxford offers last time around so only a dozen or so made it. Apparently this year is the same with lots of retakes and reapplicants making up the numbers.
Div has been a letdown. As the centre of the academic offer, it should be more than a rambling unprepared teacher at the front of class discussing the Times headline.
The teaching has been variable. One teacher taught the wrong exam for a term, another was off sick forever and English Lit results were so dreadful that they stopped teaching it and examining it rather than sorting out the underlying problem.
Has it worked out? Sure. But we wouldn't do it again today given the new direction of the school. At the price, there are many other options out there. But it will work for some.