Ash and RED do have their differences, but both also had some similarties. Ash always cared for his Pok?mon, and by doing so, created a very strong bond with them. Because of this, most of his Pok?mon don't want to evolve as evolution probably would change their attitudes. (Pikachu) Ash wasn't the person with begginners luck. He had nearly no prior knowledge of the world of Pok?mon.
Reason Ash never tries to catch legendary Pok?mon although he does get multiple chances is that he realizes why they're legendary. He knows that the legendaries have a major part in the world and by capturing them may change the world itself.
RED was a lot better off than Ash ever was! When Ash first started, he didn't know anything about Pok?mon except a few common Pok?mon names, his Pikachu never listened to him for quite some time, attempted to catch a Pok?mon without a battle, startled some flocks of Spearow, being chased by said flocks as they probably want to tear him limb from limb, and trashes a bike!
If that doesn't say that Ash desperately needed help, I don't know what does! If he didn't come across Misty, he'd probably couldn't survive the day he left! Ash didn't learn much of anything from Misty for some time, so he needed all the help he could have got, including Brock for the food and battle information!