Because what is usually expounded here is utter silliness if you really wanted to achieve this.
Telling practical political veterans we should pin everything on six-month-out hypothetical national matchup polls of a candidate who has faced zero big-league RNC attacks is grade school nonsense, as is exaggerating the differences to make Sanders look like the incarnation of leftist common sense while Clinton is portrayed as GWB's ugly more fascist sister. They know better on both counts.
But, given an SD not already jaundiced and hardened by thousands of frothing emails and phone calls sputtering the above, there are cogent arguments that might have (had) a chance.
I'd start with turnout. Clinton's safest blocs will vote D anyway. They could put my name on the ballot as the D and get 90%+ middle aged and above longterm partymember support. Sanders is stronger in bringing in new Ds. Unreliable, low turnout, low downticket impact though they are, they'll vote for him for sure and for her maybe...if they remember. Why not go for the increase in the base rather than the preference of the base that will stay loyal anyway?
I'd follow that he does match up well with Trump but not because of speculative polls. Because of "outsider" (I know, but perception is reality for many) appeal, unvarnished populism, "tell it like it is" connections and the like. Clinton better demonstrates Trump's weaknesses as a hopeless political dunce better than Sanders, but not by as wide a margin as Sanders' better job of matching up with his enthusiasm-driving, energizing and media-friendly strengths.
Then I'd go with policies. Where real differences are noticeable, Sanders' stated current policies do better with voters. Higher minimum wages. Real concrete action on healthcare, aggressive anti- Wall St controls. They are indeed tougher to get politically than Clinton's more modest goals, but the first thing is to win.
Then I would yes bring up the advantage of a candidate free from significant legal/moral/regulatory fragility. Not by parrotting RW fantasies about Clinton belonging in jail or losing clearance etc but by reinforcing how less likely RW obstruction, guaranteed to occur, is to succeed if the POTUS isn't quite as much a sitting duck for non-stop impeachment distractions and already seen as untrustworthy by the electorate.
I'd probably finish by bringing it back to GE votes but this time with Indies. Hypothetical matchups aside, Sanders does better than Clinton with Indies head to head even. We all know most Indies really aren't any such thing, but we know those who are capturable by the D have eschewed the label for some reason or another, and that they have expressed and demonstrated a greater willingness to go for somebody who hasn't been one of the ultimate party insiders for a generation. We keep the Ds anyway; why not go for maximizing the reachable Is?
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