'Organic' does not necessarily mean good for the land.
Geoff Lawton did a
video recently on the na side of organic farming which is worth a watch.
I have some concerns with this process - is your farm manager an employee? Are they leasing the land? What happens if they are no good at their job? Your whole process is dependant on these people making profits to keep the ball rolling - one bad
apple could shit the whole thing down unless you have very deep pockets.
In fifty years time who controls the land and what is to stop it being converted back to conventional agriculture?
That said there have been people in some parts of the world doing almost what you describe - buying degraded land, overhauling it using
permaculture principals to increase its fertility and value, then leave raging that to expand. Savoury style grazing systems have fantastic potential to do this in some parts of the world (Australia?)