Hi, No doubt a noob question...

Let me first say that I am not submitting this as a for sure solution that you need, and you may want to google what I am saying. However, I feel sort of confident this may be what you need.

First, your dates.

It depends on how these are written I believe. If they’ve been typed as, “24th of August” rather than, “8/24/2021,” I suspect this will throw off the sorting function. You might want to look into using actual date fields, and how to set their formatting.

Second, your sum issues.

Again, fields may solve this problem. If the numbers are just typed there it may be causing some issues even though, I admit, it really shouldn’t. Maybe make sure you use the =SUM(ABOVE) field. I assume the numbers are above and in a column. If they go into the thousands, and you have a comma as a separator, I wonder if this could also be part of the issue, which may be another good reason to use fields. 

I believe what you need to do is fix fields up for all of these things so that Word then sorts by the field data and does math using field information.