I will not go down the route of pros and cons. There has been much debate over which school is better. Both schools are excellent. If you are looking at just grades alone they are quite on par with one another, give or take. Not all parents feel that grades alone is what makes for a great school.
For your situation I would seriously think long and hard at the commute side of things. I would suggest you try doing the commute this half term perhaps to see if Olaves is do-able. Please bear in mind that as it is half term, the crowd will be a lot less. In addition, to consider that this will be on a longterm basis for 7 years to come (and much of it will be in the dark). If it is taking more than 1 hour that's 2 hours everyday that is quite a lot of time taken up by travelling.
Consider them as jobs, is it worth traveling that extra half hour one way? One may make you slightly happier but the trade off is the long commute for the very long term. Please do not forget to bear in mind that sometimes your DS will have huge amount of things to carry eg. musical instruments, sports kits, text books and the like all on the same day. There will be cricket/football/rugby matches at the school etc too where your DS will need to go to and again this will involve a long commute unless you drive him there during weekends.
In addition, there are parents evenings to consider, plays and events to attend in support of your DS... the list goes on.
What about re-locating nearer to Olaves? If its a possibility then it is not an obstacle for your DS.
Hope this helps.
THankyou for the advise. I agree commuting will be hard for the DS. I will wait for Wilson's result to come and then decide. If necessary I will surely move to Orpington.