Is there a chance I will be issued Schengen visa with longer validity than my travel/health insurance?
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I am not quite sure I understand what you are hoping for or that your strategy fully makes sense but I don't think insurance matters that much:
- If the consulate thinks you should get a visa for this one trip, it is likely to be a single-entry visa with parameters (validity, duration of stay, etc.) tracking the itinerary and evidence you submitted. In that case the ticket, accommodation and planned itinerary matter just as much if not more than insurance.
- If the consulate thinks you are a trusted traveller that should be allowed to come back to the Schengen area without being screened every time, you might get a multiple-entry visa with a long validity. In that case you are only required to have insurance for the first trip when applying for the visa so the issue is moot.
It's recommended for consulates to grant a visa with a few more days to provide some buffer in case of unplanned difficulties (e.g. with transportation) but it makes no sense for them to randomly allow a much longer duration of stay if they don't think you fall in the second category.
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