If a PARTICULAR CANONICAL HEAD KEYWORD is IMPORTANT (even perhaps a SYNONYM or LONG TAIL VARIANT) and I think a particular 301 REDIRECT has some positive impact on how Google judges the quality or relevance the page, I will make sure the CANONICAL HEAD KEYWORD and SYNONYMS are on the FINAL PAGE I redirect Google to (which is the one that will be rated and cached).
When optimising a title, you are looking to rank for as many terms as possible, without keyword stuffing your title. Often, the best bet is to optimise for a particular phrase (or phrases) – and take a more long-tail approach. Note that too many page titles and not enough actual page text per page could lead to doorway page type situations. A highly relevant unique page title is no longer enough to float a page with thin content. Google cares WAY too much about the page text content these days to let a good title hold up a thin page on most sites.

I think ranking in organic listings is a lot about trusted links making trusted pages rank, making trusted links making trusted pages rank ad nauseam for various keywords. Some pages can pass trust to another site; some pages cannot. Some links can. Some cannot. Some links are trusted enough to pass ranking signals to another page. Some are not. YOU NEED LINKS FROM TRUSTED PAGES IF YOU WANT TO RANK AND AVOID PENALTIES & FILTERS.
Ideally, you will have unique pages, with unique page titles and unique page meta descriptions . Google does not seem to use the meta description when ranking your page for specific keyword searches if not relevant and unless you are careful if you might end up just giving spammers free original text for their site and not yours once they scrape your descriptions and put the text in main content on their site. I don’t worry about meta keywords these days as Google and Bing say they either ignore them or use them as spam signals.
Sometimes, Google turns up the dial on demands on ‘quality’, and if your site falls short, a website traffic crunch is assured. Some sites invite problems ignoring Google’s ‘rules’ and some sites inadvertently introduce technical problems to their site after the date of a major algorithm update and are then impacted negatively by later refreshes of the algorithm.
This is why developing a list of keywords is one of the first and most important steps in any search engine optimization initiative. Keywords and SEO are directly connected when it comes to running a winning search marketing campaign. Because keywords are foundational for all your other SEO efforts, it's well worth the time and investment to ensure your SEO keywords are highly relevant to your audience and effectively organized for action.