You do wonder why he keeps ploughing in £600k + every month. If PNE is a drain on his resources, why is he doing this? He doesn't strike you as the kind of bloke who would be sentimental about his local football club, but then none of us know him personally (not that I'm aware of).
The endless and increasing £600k + each month begs another question: why not go the extra step to attempt to secure promotion? Just a guess, but maybe because the Premier League really is a different level financially speaking and that £600k + could quickly become millions each month?
As fans most of us just look at is as 'let's get promoted, take the £90+ million, enjoy our season in the limelight and retreat with our tail between our legs'. But it doesn't work like that in reality. It can be done though, as other clubs have proved. Money talks, you do need a benefactor and we have one.
So as you intimate, if TH is so good at planning ahead then why does there not appear to be a realistic plan for PNE to achieve promotion?
Regarding the training ground, really we should do what we were supposed to do and create the training ground on Walker Lane. I would be totally against houses going on that land.