Even if this was restated in formal terms the same deficiency you describe would still be applicable.
If the original criticism was that the phrase did not disclose sufficient information to identify the particular circumstances surrounding the search results, then the reality is that even if this information was supplied, it would not assist.
The appearance of a post in search results is not the actionable matter, but rather the underlying cause of such appearance (for example a defamatory post referring to x, which then appears in search result for x).
Here, the alleged issue was the reference to FJ on The Oatmeal's site which was in fact completely legitimate.
Disclosing the specific circumstances surrounding the search would only have served to dilute the point of the letter, which as has been mentioned was intended more as a shakedown (albeit a completely flawed attempt at a shakedown).
I also don't think he fully appreciates the complexity of how the web works. I'm sure through his sex.com case he's pretty familiar with how domain names work and the legal recourse for dealing with those, but he just seems totally out of his depth discussing libel.
As for the "punch it into Google", it's hilariously colloquial at best and ignorant of the way which Google works at worst.
On the language point, considering the nature of the language I use in my letters and agreements I draft, I found his letter to be quite refreshing (at least in terms of the language used rather than its intention!).
In terms of his awareness of the flaws, I would say that they would be apparent to most people with an awareness of the basic facts of the case. Obviously in reality, I have no idea of his awareness but I would be surprised if he wasn't.