Hi, Tom.
As the others have said, and as you apparently already recognize, withdrawing the cash is neither income nor expense, so using a Quicken Category is not appropriate to record the withdrawal. But spending the cash is an expense and should be Categorized.
Record the withdrawals as they happen. Use a Transfer to whichever other Account is appropriate. Transfer the cash to Checking Account, if that's where it went. Or to your new "Cash Personal" account, where it will stay until you record what happened to it after that.
You can categorize the expenditures in detail, or in batches, or in a lump sum - the choice is up to you. I'm one of those "micromanagers" like Fred's Dad (see later in this thread), but I only count my cash weekly, not daily. If you simply can't remember (or don't choose to record) what actually happened to some of it, then put it in a Category with a name like "Tom - Miscellaneous" or "Wasted!" or whatever makes sense to you. The important point is that your cash account balance be kept at or near the actual amount in your pocket, at least at the end of any reporting period you choose. And that all expenditures get accounted for, even if they went to "Can't Remember". If the cash is gone, it either went to some other Account (New TV or Investments or Checking - or Loan Payable) or to some Category (Groceries or Gas or Ice Cream Cones or Tom - Lost? or Other). The names of the Categories are not important - except to YOU. (And to your wife? Who else is going to read your Quicken?) Unless some of the expenditures are deductible on your tax return.
Another choice that many people make is to simply collapse the two transactions (withdrawal and expenditure) into one entry in Quicken. When they withdraw the cash, they put it directly into the "Tom - Personal Expenses" Category. This not only loses the details of "where did the money go", but also obscures the fact that there were actually two transactions for each amount withdrawn and spent.
RC