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I would work on it now, because it gets harder when they're bigger and stronger!

There really are countless ways to teach loose leash walking. If you want the pup to be in heel position at all times while walking, I would lure the pup into the position and reward him for being there. When he breaks out of that position, stop moving, lure him back, reward him, then continue, rewarding frequently when he remains in position. At festivals and whatnot, it may be too much for him to be learning. He's so overwhelmed with the excitement that he's simply over threshold and beyond paying attention to you. I would start in more quiet parks with minimal distractions to work on it, then move up to more crowded areas. Look up Kikopup or Zak George, I liked their versions of teaching LLW.

It's also common for dogs to be able to perform in one environment, and not in another, because they don't generalize well. At home or at the training facility the dog has been heavily rewarded for performing correctly. Out in public is a different matter, and the distractions are real and random, so its important to reward well when you do encounter a distraction!

I would not repeat "heel" over and over and over again. You're poisoning the word. Or perhaps he doesn't really know what it means, so you're just teaching him that heel means PULL ALL THE PLACES THEN GET TREATS.

As for greeting people, you can teach a "default ignore," meaning the dog just ignores people on walks, or you can teach him that he has to do something for the person to greet him, like sit and be calm. If he can't, then the person goes away. It's up to you, it's your dog. I think you're pup will probably be fine if he doesn't greet people while out and about, just settle for people you invite to your house, or at class.
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