Surely he would check it was going to be approved, unofficially, before he went to the hassle of proposing and then getting official approval. Its not like he doesn't know the Queen, he knows whether she approves of his relationship or not.
Either there is already tacit approval in the family and this will go ahead or he is already aware that, because she is divorced, they won't be approved and that this isn't really going anywhere.
has she appeared naked in any of her shows? They don't like that. But on the other hand - its 2017 and this is an archaic ritual that has to be done but doesn't really mean anything anymore. I certainly don't think the royal family would dare openly disapprove, their popularity would plummet.
he is fifth in line to the throne so surely the wedding won't need to have as much pomp and circumstance as William's.
Both Anne's and Andrew's weddings were televised. If they're lives aren't being televised for the masses, what's the point of them? I think the privacy ship has sailed and they sort of have to accept that, Harry might want privacy, doesn't mean the Palace will allow it.