Hi Hap',
There are two routes you can follow to do this—using a formula, or using the Categories feature of Numbers.
Here's an example, using the formula approach:

Expense Ledger is your Ledger table.
There are no formulas on this table.*
Column A contains the date of each transaction. This must be a Date and Time value, but is entered as 'date only'. Numbers automatically sets the time to 00:00:00 (midnight at the beginning of the date entered).
I've omitted the data in column B, as it does not enter into the calculations.
Each cell in column C contains a copy of a pop-up menu containing the names of each category you are using. The Pop-up menu is set to 'start with a blank', as can be seen in row 10.
Column C contains entered data, the amount of each expense transaction.
Summary by Month is your Summary table.
The table contains one formula,** entered in cell B2, and filled down and right into the rest of the cells shown. The formula is shown below the two tables.
The dates shown in row 1 are the first day of each month, and must be Date and Time values with the time part set to 00:00:00 (by Numbers) and not displayed, and the Date part set to the first day of the month in each column . Numbers is a bit picky in matching dates displayed in different formats, which is what led me to include the Day (01) in each display.
Formula in B2:
SUMIFS(Expense ledger::$D,Expense ledger::$A,">="&B$1,Expense ledger::$A,"<"&EDATE(B$1,1),Expense ledger::$C,$A2)
This is a SUMIFS formula which sums the values in column D of Expense Ledger, including only the values in cells on rows where all of the following are true:
- the value in column A is later or the same as the date in B1 of Summary…
- the value in column A is before the date one month after the date in B1…
- the category in column C matches the category in this row of column A (of Summary…)
Results are as shown on the table.
*I also used a formula to enter a series of random (but increasing) dates in column 1 of Expense Ledger, but this does not enter into the functioning of the table.
**Dates in cells to the right of B1 were calculated using the EDATE function shown in the formula. If you choose to use this function for this purpose, I'd suggest replacing the formulas with the calculated values before using the spreadsheet. there's no point in recalculating these formulas each time a change is made to the table—they are static values, changed only once a year.
Regards,
Barry
PS: Categories is not available on my older Mac, but I would expect to see a Categories solution offered here before long.
B.