Here's an odd proposition for you... (sorry by the way, the Rodney Walker thing is fresh in my mind and I'm trying to get my head around possible scenarios)
Rodney Walker donates 165000 to Wakefield to pay the tax bill, upon the share thing being announced it gets turned into a loan - If 500000 is raised to own 50% of the club, then this effectively values the club at 1 million. Rodney Walker does not then take the cash out of the club but instead converts that loan into shares and at no further cost to himself he gets 16.5% of the company.
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