So it will read columns B & C, Everyday > Groceries on the Statement sheet and that amount will automatically go into the Expenses sheet in the correct place. And also read the date and put it in the correct month column.
Check this sheet (Make a copy for full access)
Helper Pivot tab, which is referenced by formulas in Expenses tab. You can hide that tab in the final spreadsheet.
=iferror(GETPIVOTDATA("SUM of $",'Helper Pivot'!$A$1,"Category",$A3,"Date - Month",text(D$2,"MMM")),0) can be copied/filled right or down as you wish inside the