This is definitely an annoying problem and I don't have a root cause or permanent fix for it. But I have a workaround that seems to solve the immediate problem on a per-account basis.
In short, delete the local user profile. What I have observed is that the only things that get properly indexed from the Start Menu are things that existed when the account ...
I FIGURED OUT A SOLUTION.
I wanted to share my final query, along with some important lessons I learned along the way.
LESSON 1. HOW TO IMPLEMENT MULTIPLE PARENTHETICAL STATEMENTS
You can only use one parenthetical in a query. However, you can nest another set of parentheses inside that query.
Ex: -SearchQuery "(a OR b) AND (c OR d)" WILL PRODUCE ...
The option you mentioned is directly related to the windows search service.
It is greyed out when it's not installed.
Try using "Content:" or the corresponding word in your servers language in the search field, it will still find files with specific text content, although without indexing it might take some time.
Sorry for necromancing, but unanswered ...