Hi Kip!

I found one solution to totaling items in a table based on their checkbox option:

$(document).ready(function () {
  
    $('.cf-table-block').on('change', 'input', sumtotal);
    function sumtotal() {
      
        var estimate = 0;	// The "Estimate $" value
      	var estimateTotal = 0;	// The total of each "Estimate $" value in the table
      	var federalTotal = 0; 	// The total of each general "Estimate $" value in the table
      	var generalTotal = 0;	// The total of each Federal Grant "Estimate $" value in the table
		
		// Goes through each row in the table
        $('.cf-table-block tbody tr').each(function () {
			
		  // Set the estimate for each row
		  estimate =  parseNumber($(this).find('.sum input').val()); 
		 
		  // Find the checked boxes in each row
		  $(this).find('.checkbox input:checked').each(function () {
			
			// Add estimated value to the General Grant total if checked
			if($(this).val() == "General"){
			  generalTotal += estimate;
			}
			
			// Add estimated value to the Federal Grant total if checked
			if($(this).val() == "Federal_Grant"){
			  federalTotal += estimate;
			}
			
		  });
            
			// Add each row's estimated value to the total
            estimateTotal += estimate;
        });
		
		// Populate totals
        $('.total input').val(estimateTotal);
      	$('.generalTotal input').val(generalTotal);
      	$('.federalTotal input').val(federalTotal);
    }
  
    function parseNumber(n) {
        var f = parseFloat(n); //Convert to float number.
        return isNaN(f) ? 0 : f; //treat invalid input as 0;
    }
});

And here's what my example form looks like: 

This code will go through each row in the table and total the "Estimate $" values into the Estimate $ field (regardless if any checkboxes are checked).  It will also add that Estimate $ to the General Fund if its corresponding checkbox is checked, and/or add to the Federal Grant total if the Federal Grant checkbox is checked. 
For this code to work, I also added CSS classes to the following items:

• Class sum to the Estimate $ table column.
• Class checkbox to the Funding Source table column.
• Class total to the Estimate $ field (outside of the table).
• Class generalTotal to the General Fund field.
• Class federalTotal to the Federal Grant field.

To add a CSS class to a column in the table, select "Field options" in that field in the table:

Then, go to the "Advanced" tab and enter your class name:

Hopefully this gives you a good starting point for getting the functionality you're looking for.  One difference I noticed was that you had your funds in a table, whereas mine are in individual fields.  By applying the same CSS classes to the table items, you can accomplish the same functionality. 

Also, by adding another column and giving it a CSS class, you can modify this code to pull a value from a drop down and put it into a text field.

I hope this helps, and check out our Forms online documentation for more code snippits and JavaScript help!

Madison