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So, I'm right in thinking next season is the last in the 5 season plan?
Would Clarke commit to another 5 whatever the outcome of next season? Doubtful.
If we aren't promoted, it seems unlikely he'll commit to more years of loaning TUFC money. A million a year is it we're losing? If so, who will come in, pay him the money owed and commit to pumping more cash in?

If we're promoted, would he push for the new stadium? Or decide this is the optimum time to recoup his money.

I feel Gary is by far the best manager we've had since Leroy, and our best chance at promotion. But again, I assume next season is his last contracted to us.

So is next season one of the most important in our history?

The five year plan originally envisaged a new stadium then when it became clear that wasn't going to happen the target became promotion to the EFL and that doesn't look like happening.
Osborne won't get his £4 million back because no one is going to pay that for the club, in fact I don't think anyone would seriously consider buying it. So likely scenario is Osborne walks away and the pad locks go on the gates, the same situation the Dean Edwards/Dave Philips consortium faced.
So basically I think it's promotion or bust next season.