Would Daniel have Beaten Bobby?

Yes
The script called for it.

Since Johnny was obviously the pride of the Cobra Kai and Daniel beat him, I'd say yes. Though he may have had to pull out the crane kick early, which would have made it impossible to do later against Johnny.

Creese was probably observing Daniel's technique and realized it was better than he had originally figured. He knew Daniel would beat Bobby. That's why he told him to take him out the way he did.

Same as with Johnny; in the tournament, yes. In a street fight no.

Daniel's limited training was honed for defensive tactics. Keep blocking points until an opportunity for a point.

In reality Daniel-san would have been put in hospital by the Cobra Kai's well before ever getting anywhere near Daniel being able to train.