Thank you for the response! In an attempt to better explain my question I believe I overcomplicated it ...
Your response is helpful, but also triggered more questions in addition to the ones I had.
Here are questions I am still working on addressing:
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Your title tag example struck another question for me. Currently, we use the same structure which would be summarized by "Keyword | keyword version 2 | Brand/Company Name". Based on my understanding of Rand's recent Whiteboard Friday: https://moz.com/blog/one-hour-guide-to-seo-keyword-targeting-on-page-optimization this would not be considered best practice anymore. Rather, your title would be written to say Fast Car Insurance Quotes online with Example... It's not just keywords and brand, it's compelling, etc. Here is another supporting article: https://moz.com/blog/title-tag-hacks-whiteboard-friday Thoughts on that?
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Based on almost all guides findable and the fact that WordPress auto-populates the H1 with the page title, does the page title need (or should) to match the meta title tag?
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Does the menu name need to match the page title? In your case - the menu name itself (assuming in the main menu) does it need to include the longtail version. In other words - how much impact does the menu title itself have on SEO? If any? And does it need to match the page title/H1?