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Ok. So to get the chart based on "Current Year" and showing a single column for every month Jan - Dec and adding up the appropriate amounts based on start and end dates, here is what we need…

In a separate sheet, put the month labels in the Primary Column.

January

February

March

so on and so forth

The next column will be a text/number column called "Month Number", and you will manually enter the month numbers.

1

2

3

so on and so forth

Then you will have a text/number column formatted to show currency and using this column formula with cross sheet references:

=SUMIFS({Monthly Savings}, {End Date}, @cell >= DATE(YEAR(TODAY(), [Month Number]@row, 1), {Start Date}, @cell <= IFERROR(DATE(YEAR(TODAY()), [Month Number]@row + 1, 1), DATE(YEAR(TODAY()) + 1, 1, 1)) - 1)

You are also going to need to use one of the various solutions for keeping the TODAY() function up to date. My personal preference is to insert a dedicated date type column and have a record a date automation running daily and recording the date in this dedicated column.

The helper column may not be needed depending on exactly when you want to trigger though. If you set your trigger to be date based, you can set it to "Run Once" and change the "on" to one of a handful of more common selections including 60 and 30 days before a certain date field. The helper column comes into play if you need something a little less "standard" such as 10 days or specifying working days.

Thank you @Paul Newcome and @Nitish K! I was hoping the automation wouldn't need a helper column but looks like that's all I can do. Appreciate you both!

On your beautification note- I get the same thing with my notifications. I have to pare down the columns from "all fields" to "specific fields" and then things are easier to read: