I'll add that I'm confused by your statements here. In the US, §107.51 requires staying below 400 ft AGL (= above ground level), so what do you mean by "NOT specifically answered in any Ruling". Are you arguing that the term AGL is not clearly defined, that US law doesn't apply until it has been tested in court, that this law doesn't apply to §101, or something else?
Not arguing with the 400ft above ground ... we have similar ruling over here as most countries do.
The question is what happens as the AC moves away from the hill top where it was launched, as in OP's first post.
This is where others have ignored the moving out from the hillside and over the valley.
My original reply was not a statement but a suggestion that anyone standing in the valley with the AC now above them would regard it as being higher than the person who is looking at his Go display after take off from the higher point. A fact that has been subject of debate I know in various discussion groups including LARPAS, which I am an active member of. The debate has been further muddied because of many peoples interpretation despite numerous cut and paste links by various.
There are the 400ft over top of any structure - even a mast ... 400ft over ground ... 400ft allowed out to 400ft horizontally from a structure .... the list of possibles goes on and on. The fact is the simple statement of 400ft AGL has led to debate not only on forums but also in Govt appointed groups such as our LARPAS. Look at AMA and FAA ... CAA and BMFA (actually BMFA and CAA have got closer to agreement than any other !).
I was illustrating that the Pilot will regard his AC as still at 100ft as example referenced to Home Point, but the other person 400ft below in the valley who now has the AC above him would say the AC is now at 500ft ... and could, if that person was an efficious son of ****, lead to authority action.
AGL is AGL we all accept that ... trouble is DJI has not given us a tool to keep to terrain following AGL. DJI data of our flight - the only true AGL is over the home point.
The OP was asking how to do it. Because as a person in the street - he's obviously unsure what is the real answer. As it appears are many others ...
I do not profess to know the answer of how to satisfy the AGL limit when the ground is not level - as I say - its been a debated subject in LARPAS and because of the tools we have in hand when we fly creates a difficulty to determine actual AGL through the flight.