From memory the "Aldershot Special" only works from certain stations down the east, also only valid if the train stops at Clapham Junction (unless one of the tickets is a Zonal ticket or a season ticket).
3 days used to be the point where it is cheaper to get a weekly season ticket, have a check on the National Rail website to check the price of a weekly compared to 3 day tickets.
To complicate things further it's not the departure time that determines whether it is Peak, Off Peak or Super Off Peak but the arrival time in London.
Arriving after 09:55 is OP, arriving after 10:55 is SOP, no restriction on what time you leave London on an OP but there is for SOP. I doubt...
Unless they've changed the rules since I was selling them it depends when he is traveling. If it is after 10:00am then it's perfectly fine.
Not that I know when Bozza is traveling.