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He'd be in the pack. There are too many people frustrated with the Democrat field, as well as a certain group that would love his celebrity status. He may not be liked by establishment democrats, but he would pull support from them, as well as pulling others generally frustrated with DC politics. (Maybe even carving off some Sanders supporters).
If you think that establishment democrats despise him, just wait until you get a load of what progressives in the party think about this neolib, self-interested opportunist. His only allies are a minority of centrist/establishment Dems and that's precisely his problem. He may do better if Biden melts, but will be completely impotent until then.
If it appears Bloomberg's serious, I think he'll easily eclipse Steyer. But I have no idea how high would indeed go.
As per above. Again, the only way he's going to do well is if he somehow convinces moderates who don't already despise him off of Buttigieg and Biden's ships.