Q:Is it conceivable that a single engined helicopter would get approval to fly over a congested area, with the intention of landing at a confined helipad within the area?
IMHO no chance that he would get approval for a CAT flight. Many Privateers think that the ANO doesn't apply to them, though, and do what they can get away with.
I think the CAA have trouble enforcing rules in court and may shy away from it after they lost the case against the Clacton Pier Cowboy a couple of years ago.