Aris Skript assumes, that you apply ‘Day entries’ and ‘Date headings’ by hand. I’ve no idea, why he collect first insertionPoints and did it this way …
What I did manually:
1. This is clear.
2. Find the beginning of a paragraph, followed by a number, that consists of 2 digits, followed by a uppercase letter. This will find 22 Monday’, but also ’99Chicken wings’. Since I didn’t find those chicken wings-problems in your document, I decide to do it the easy way. Otherwise the search must be more specific.
3. (?s) choose the so called ‘Single line mode’ and affected the scope of the wildcard ‘.’ So in this special case, it finds a character with applied style ‘Day entries’, if the next character has not this style applied. So it finds the last line and give us the chance to apply another style.
To your last question:
Sure, this could be done by F/C or could be part of a grepstyle: (?i)week\x20\d+$
Will find caseless week(WEEK), followed by an space, followed by any number at the end of a paragraph.
best
Kai