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One obvious answer is to google seo and the town you are in e.g SEO Seattle and see which companies have managed to get themselves optimised for that. If any companies look promising try searches like company name scam, company name problems, company name reviews to see if there are any known issues with the company.

In a lot of cases I optimize the same page for several related keywords - like in your case. The only thing I follow is to place a tier one keyword and tier two, three related keywords and know/ be sure which one is which so the plan is crisp and clear. I usually optimize more for the main keyword and I use most of the on-page optimization for this particular keyword. I optimize tier two and three on the same page without cutting any modules from the main one (using some h2,h3 maybe and to be sure the page has a good % of the main keyword first and then the second and third tier ones.) The anchor text for links that will point to this page will vary and I think that is a good thing - a natural thing and it will help overall including your link diversity. It's better to have more anchor text with the links for your page and not only "student health insurance" as anchor text. Overall is a natural thing to rank for more then one keyword especially for long tail variations. However, that's just my opinion. I do that a lot in my optimization sessions and the results so far based on this strategy are good. Hope it helps.