#3) I do need to go back to basics upon further reflection.... he isn't pointing in the backyard so why should I expect him to do it in the field? I can have him on the check cord, have a dead pheasant back there and have him "Whoa" before he gets to the bird and he will honor that but he won't lock up on point without the check cord and me saying "Whoa"....
A dead bird isn't the greatest way to work on steadying a dog. But if the dog has never pointed a live bird without you saying "whoa" you may have other problems on your hands (the instinct may just not be there, it happens).
Whatever the case I would put away the shotgun and get the dog on birds, lots and lots of birds, and see if he can learn from his mistakes and start pointing. Stop saying "whoa," it's a worthless command when the dog is any distance away, and let the dog learn.
Regarding hacking with the e-collar. If you're having to use it a lot the dog isn't ready to be hunted. It's acceptable to teach the dog how to handle that way but you want to make sure the dog has it down before hunting with him. You also want to be careful not to kill its drive. This is best done in areas relatively free of birds. It is possible that you've exacerbated other problems and turned the dog into a blinker.
I would recommend finding a good trainer to help you out.