As I see it, the issue here is whether one can advertise cost-shared flights
on a website, when the ANO says they may be advertised only within a flying club.
I don't think anybody is suggesting that the cost sharing percentages would be exceeded - that would be straight illegal public transport. Yes of course it goes on, all the time, but is a separate issue.
As regards genuine friends, not many of them will be genuine friends if they have lost their legs and stand to pick up a £1M passenger liability payout by claiming that they had agreed to contribute something exceeding the cost sharing maxima
Or, of course, if they are dead and then their estates will be going after you and will be completely happy to strip you bare (vis. Graham Hill, etc), leaving you with just the legal minima for a personal bankrupcy (underpants, cutlery, not a lot else).
Even when there are no injuries at all, a spiteful associate can drop you in it. There is a well known helicopter pilot/instructor who got done for illegal flying, only because he had a dispute with a customer, the customer shopped him to the CAA, and the accused chap was an upright individual and admitted it (personally I think he should have just said the payment was for "ground school").
Getting back to the "website = flying club" I don't think this will ever be settled until (or if) somebody gets done, and I bet you anything the CAA will not want to test this, because if they do, and lose (which I reckon they would) then it would open the floodgates to all kinds of illegal charter, booked via the internet where nobody will be able to keep tabs on it. As things stand, you have the
FUD of the "flying club" and nobody wants to see if they can push it.
It's like whether a GPS can be used in place of a DME. The ANO uses the words "distance measuring equipment". Now, we all know that a GPS cannot give you the distance to a point
I bet you the CAA will never want to test this one, because if they lose (which I reckon they would, unless your lawyer is really useless) they will end up with a US-style universal GPS-DME substitution precedent. OK, we all know that de facto that is already the case in RNAV airspace but.....