It as you say Middlefordiddle that CH was buying Bill Quinn's share from him them he should have paid for them out of his own money.
If the monies paid to Bill Quinn for his shares have been paid for by the club itself they must be deemed to have been bought back by the club and are now cancelled shares. They cannot be re issued.
As the club is a Private limited Company it is governed by certain rules.
I believe that In addition Companies House should have been informed that the club is taking this action and must state that the club will not become in danger of insolvency by spending money this way.
I believe also that the clubs creditors must be informed as well of the intended action as they might argue that they want paying before a club takes that action.
The clubs only issued shares must now be the ones held by the other shareholders apart from Bill Quinn.
I believe that Bill Quinn held around 75% of the shares with the remaining 25% held by the other shareholders. As the original Share capital was some £50,000 , and those percentages of issued shares being correct the issued share capital of the club would be around £12500.
If that is so, the club is in a very bad situation. Shares of £12500, debts in excess of £200.00 according to the last set of accounts, who in their right mind would invest in the club in that financial situation, with a ground that needs £0000,s spending on it to get it to a decent standard.
It his not much of a business proposition and doing it out of loyalty, or whatever you would not be left with much change out of a quarter of a million pounds.