A socialist will not be perceived as a moderate by American voters. Especially when compared to a conservative governor who has a strong record on governing a swing state.
See, you're using real life logic. That doesn't apply here on Atlas.
Bernie Sanders isn't any more socialist than a lot of other mainstream government officials (including Obama before he became President); he's just the only one that identifies himself as such. If he is able to convince American voters that democratic socialism is different than USSR-style socialism through a public awareness campaign, he has a great chance of winning the election by a sizeable margin. I think somebody made this point earlier, but people would actually have a reason to be inspired to vote for Bernie Sanders (REAL change); Jeb Bush is just some status-quo mainstream Republican who would disenfranchise many, especially including those who are actually looking for change. And Sanders won't be burdened by comparisons to Obama or the mainstream Democratic Party, as, well, duh.
1.) Sanders is going to be spending much of his campaign on defense. Bernie Sanders is going to need to run a public awareness campaign before he can even think of winning. This is an added barrier to winning that he simply can't afford.
2.) Your strategy for Sanders relies on the effectiveness of a fairly complex and nuanced argument. Can you see the problem here? Complex and nuanced arguments get lost in the noise.
3.) Bernie Sanders is going to spend much of his campaign talking about how Socialism isn't so bad, meanwhile Jeb Bush will line up Republicans and conservative Democrats to talk about how Socialism
is that bad. A public awareness campaign is impossible if its swamped up in ads saying the exact opposite thing. Most voters will write it off as 'he said, she said' and just go with their already existing opinions.