Obi-wan on Tattooine during Episode IV

I hope I'm posting this in the right place as the answer can't be found in the film, but did Obi-wan frequent the Jundland Wastes, and if so, why, or was this just part of his promise to keep an eye on Luke?

It makes me wonder about perhaps other times Vader's former master rescued Luke from peril while remaining out of the picture. It's kind of a funny idea, whether Obi-wan was an adrenaline junky preferring dangerous places (the reckless old coot!) or just keeping Luke safe (that kid is a handful!).

Extra points for knowing if Luke exhibited any Force ability prior to his encounter with Obi-wan in the JW.

Anyway, any info, opinions, references?

Thank you for your time, I love this stuff!

 

The book with the most Obi-Wan/Luke interaction is The Life & Legend of Obi-Wan Kenobi. We can see Owen's hostility growing over time:

While Luke's still a baby- when Owen's decided he doesn't want Obi-Wan to hang around too much:

"Hello, Owen," Obi-Wan said as he brought the eopie to a halt. "Is something wrong?"
Owen nodded once. Obi-Wan began to dismount, but Owen held up one hand and said, "Don't bother. What I have to say won't take long."
Obi-Wan kept his eyes on Owen as he shifted his weight back onto the eopie.
"I'm not sure how to put this," Owen continued, "so I'm just going to say it. The way you come around my place ... it bothers me."
Obi-Wan sighed. "I'm sorry, Owen. But as I told you, I need to make sure the boy is—"
"Wait," Owen interrupted. "My wife and I are the ones raising Luke, right? That's what we agreed to?"
Obi-Wan nodded as he wondered where the conversation was going.
Owen said, "Well, I didn't agree to you checking on us daily, let alone twice a day. I don't mean any disrespect, but I've been keeping Tuskens off my property for years and ... well, I just think you coming here so often is just a bad idea!"
Keeping his voice calm, Obi-Wan said, "Owen, I assure you, I don't question your ability to handle the Tuskens. But as we've already discussed, it's not the Tuskens I'm worried about."
"Oh, right," Owen continued. "It's the Empire. But then let me ask you something." Owen swallowed hard before he continued. "If you're so concerned about the child's well being, why don't you try staying away from us? Didn't you ever think what would happen to Luke if the Empire tracked you down and found you living in my back yard?"
Owen's words left Obi-Wan momentarily dumbstruck. Then he shook his head and said, "Forgive me, Owen. "You're absolutely right. I'll be more careful. More discreet."
"That's a start," Owen said. "Again, I don't mean any disrespect, but ... my wife and I can't raise Luke in any ordinary way if we know you're always lurking about. Understand?"
"Yes," Obi-Wan said. He expected — maybe even hoped — that Owen was going to say something more, but when he didn't, Obi-Wan said, "Good night, Owen."
Owen nodded once again, then turned and headed for the entry dome. Obi-Wan turned his eopie around and guided the creature back across the desert.

Not long afterward: after Tuskens (led by a "Tusken" with two lightsabers) start attacking nearby settlements:

Owen glanced back to his own home, then returned his gaze to Ben. "Normally, I'd tell you to get lost. But I just got word from a friend in Bestine. The Sand People attacked another farm." Owen looked away again. "Only one survivor," he continued. "A little girl. But she didn't last long."
Ben sighed. "I'm sorry, Owen."
"I'm not finished!" Owen roared, his eyes now blazing at Ben. The edge of Owen's upper lip quivered nervously.
He's not just angry, Ben realised. He's terrified.
Owen licked his lips before he continued. "The little girl ... she said she saw one of the Sand People, maybe their chief. She said he ... he used two 'laser swords.'"
Over the last three days since Ben's last exchange with Qui-Gon Jinn's spirit, Ben had had plenty of time to consider the possibility that A'Sharad Hett was involved in the recent killings. Still, hearing Owen's description of the marauder's leader made him feel suddenly queasy.
Oblivious to Ben's discomfort, Owen said through clenched teeth, "I don't suppose you've heard about any missing lightsabers on the planet, Mr Jedi?"
"Get a hold of yourself, Owen," he said, keeping his voice calm. "You know I had nothing to do with the attacks."
"Maybe not!" Owen said bitterly. "But I have some idea of what Jedi are capable of!"
"You're talking about Anakin," Ben said, "About what he did after he learned that his mother had been taken by Tuskens." It wasn't a question.
Owen winced, then he scowled at the ground. "Shmi Skywalker was a good woman." he said. "We tried to rescue her, but my father ..." The words caught in his throat, and he left the sentence unfinished. Tilting his chin in the direction of the entry dome, he continued, "When Anakin brought Shmi's body home, I'll never forget the look on his face. If killing me would have brought her back to life, I know he would have killed me then and there. I could see it in his eyes."
Ben grimaced. "Anakin never told me what really happened, Owen. Please trust that what he did that day was not the way of the Jedi."
"Well, I'm not so sure if that's a relief," Owen said. "Much as I didn't like the way he looked at me, I like the idea of Tuskens with lightsabers even less. There's not a person on Tatooine who wouldn't be happy if all the Tuskens were dead."
Ben offered no response. He knew that the deaths of Tuskens would not bring him any happiness, but he didn't believe there was any reason in explaining this to Owen.

Some time later, after Obi-Wan brings Luke home safe when him and a friend wandered far from home and ran into a krayt dragon:

"This is Mr Kenobi!" Windy gasped. "He saved us from a krayt dragon!"
Windy's mother looked up at Ben and said "Thank you, Mr Kenobi!" Windy's father patted his son on the back as he smiled gratefully at Ben.
Ben returned the smile sheepishly, then looked to Owen. Owen glowered at him.
Luke arrived at Beru's side and exclaimed, "Mr Kenobi told us stories about living on the Dune Sea ... it was great! Can he stay for a while?"
Without hesitation, Owen answered firmly, "Mr Kenobi has to leave now."
There was a moment of awkward silence. Then Beru, clearly outraged, glared at her husband and said, "Owen Lars!"
Ignoring his wife, Owen stepped forward and grabbed Ben's upper arm. "I want you off my property," Owen said, "and don't come back!" He gave Ben a shove.
Ben stumbled back but instantly regained his balance. Looking away from Owen, he faced Luke. Ben had hoped to talk to Luke, who looked positively stunned by Owen's behaviour. Now all Ben could manage was a slight, sad smile for Luke before he turned and walked away.
Back home to the Jundland wastes.

In the Black Fleet Crisis books, there's a reference to Luke using the Force, unconsciously, to locate a missing object - and Owen giving him a yelling-at- as if he was the one who hid the object in the first place. After the fact, a much older Luke has come to realise that this was Owen fearing that Luke using the Force would draw unwanted attention - maybe from the Empire.

 

There is also a Tales story which deals with this, but I cannot remember the title.

 

Sandstorm:

http://starwars.wikia.com/wiki/Sandstorm_(comic)

however, unlike the various other versions of "Luke runs into krayt dragon", Windy and Obi-Wan aren't present.

 

Ow wow, that was awesome! Thanks people, I'm going to check out those books, pronto. Iron_lord, thanks for the exhaustive effort! General Immodet, I'll check out Sanstorm. Thank again, guys!