Hi toobusytothink.
My DS currently attends Wellington and is very happy there. He is not at all sporty but is highly academic (in top 1% for intelligence in the UK) and is being challenged very well in all subjects. He had his pick of the most well known public schools but chose WC. He's a full boarder and often enjoys spending weekends at school as we live almost 100 miles away (not in London).
I've met the Master several times having received a number of personal invitation to special events. Most recently I was invited to lunch at the Master's Lodge on Speech Day and to the official opening of the Living Legacy Garden (featured at the Chelsea Flower Show in 2015 and now rebuilt on the school grounds). I also accepted an invitation from him to attend an event at the Duke of Wellington's London home. He has always been very friendly, approachable and confident and is clearly passionate about his role as 14th Master.
I can't comment on his popularity among his colleagues, staff, the pupils, parents, etc. but from what I've heard from other parents and from what I've witnessed, he is definitely committed to making the school the best it can be. Let's be honest...he has some pretty big shoes to fill after AS and while I definitely think he has the potential to do just that, I think it would benefit the school even more if he simply continues to make his own shoes fit comfortably.
As for what other parents drive...I wouldn't allow that to influence your decision as to whether your children should attend Wellington College or any other school. The quality of education, teaching staff, facilities, opportunities on offer and how your children feels about the school are what, I personally think, matter most.
I think it's a great school. Good luck!