The vast majority of men are incredibly easy to outcompete. Start by not being an asshole to her and about 90% (or more) of the competition will be eating your dust right out the gate.
Saying "Hey, how are you?" does make me an asshole?
It depends on the context and your intentions.
No, just an uncreative generic guy like the previous 99 that messaged her pretty much the same boring question earlier this week.
Can you give me an example of a "creative" message that you could send to a total stranger that you have 2-3 images of, that are not compliments regarding their looks?