The "gap" between reconciliation and payout of member withdrawals.
Ruth asks a very good question.......
This last year, we had five members withdraw at, or around,the same time. The actual "bookkeeping function" was, of course, simple. The payout sum had been calculated; the members notified. Then came the wait! We had all DRPs for our holdings and had to await the payouts anywhere from 6 to 8 weeks. When the monies finally arrived, the members were paid in full. However, by the time the "cash" arrived, the market had fallen. We were left with the original figure and had to pony up the extra cash. How does one handle the "gap"? Or / and should we have calculated in some other fashion?
As you've discovered, paying off withdrawing club members can become a very complex issue.   It is an issue that is best discussed by the club membership and addressed in the club's  partnership agreement well before the first member ever withdraws.    With a little forethought and advanced planning the process can be done easily, effectively, and fairly to all parties concerned.
Problems arise, as in your case, when the actual payout is made on a date later than the date used to determine the value of the withdrawal.   This means that the value of the club and/or the assets used to pay the withdrawal have either increased or decreased in value since the payout amount was determined.   The question then becomes, who should reap the benefit or take the loss associated with this change in value?   Should the withdrawing member take the loss simply because the club was unable to raise funds in a timely manner?  Or should the rest of the club membership take it on the chin simply because someone decides to withdraw?  On the other hand, what happens if the club's unit value goes up?  Who should benefit?   The club or the withdrawing member?
First, let's consider a cash payout, as in the above mentioned situation.   In my opinion, once the dollar amount of a cash withdrawal payout has been set , the withdrawing member is entitled to that dollar amount, regardless of when the money is actually transferred.   If the value of the club goes up or down after the withdrawal has been valued, that gain or loss is realized by the club, not the withdrawing member.   Let me reemphasize, that's only my opinion.   Your club's partnership agreement may define the payout in any manner agreeable to your club's members.
What about withdrawals paid with stock?   Who takes the hit or reaps the gain when the price per share of the stock being transferred goes up or down between the valuation of the withdrawal and the date that the shares are actually transferred?   Again, there is no one right or wrong answer.  It is an issue that should be addressed and a policy defined in your club's partnership agreement well in advance of the first withdrawal.
In any case, the most straight forward solution is to pay off a withdrawal immediately after the date in which the withdrawal is valued.   How does a club do this?   Generally, most clubs define a period of time, usually a month, between the date in which the withdrawal notification is presented to the club by a withdrawing member and when the withdrawal is actually valued/paid.   If the club has done a good job in following its investments there is little reason for waiting a month or two, even longer in some cases that I've heard of, to make a decision and to initiate the payoff.   As soon as the club receives notification of withdrawal, the club can initiate the process of selling enough investments to raise the required cash, obtain commitments from remaining members to make payments to the club so the club has enough cash on hand to pay off the withdrawal next month, and/or initiate the transfer of stock to withdrawing members.   Even in the case of some DRIP's, the sale of stock or the transfer of certificate shares may be initiated in a timely manner via phone or online without the need for slow snail mail.   Advanced planning and staying informed as to the requirements of your broker or transfer agent is key in making the transfer process run smoothly.
The most complex and often the most beneficial method of paying a withdrawing member is via the transfer of appreciated stock to the withdrawing member.   When handled timely ,and in the proper manner, the transfer of appreciated stock to a withdrawing member is a win-win situation for both the club and the withdrawing member.  For more information on handling the transfer of stock please see the column that I wrote titled "How to transfer stock to withdrawing members of a club".  
Also, you may find the following articles of value as you consider how to best handle withdrawals in the future.
In conclusion, withdrawals are best handled where the payout is done in conjunction with the valuation of the withdrawing members account.  If there is going to be a delay between the valuation and the actual payout, the terms of that payout should be clearly defined in the club's partnership agreement.
Jerry Dressel
St.Louis, Missouri