I have no idea on why you would want to un-train your dog from seeking permission before he eats. I have purposely trained Lola to do that as well as when she leaves with me walking her she is to wait until I say she can leave when I exit the door first. Same on returning, she needs to hear me say come on before entering the house after I entered first. In addition I have taught Lola that when I place treats on the floor she is to wait until I tell her she can have them and at that point she can only have the one I am pointing to.
With your dog eating three bites of his food and then seeking your reassurance are you sure he even likes his food? Try hiding a treat under his food to see if that makes a difference. You might find that he takes more than 3 bites trying to get to the treat in the bowl. If that is the case then perhaps he does not like it.
As for your dog being clingy and needing to be near you all the time you need to start training your dog to be more independent and have more confidence. You can do that by taking small steps and leaving the dog on his own. Start by being in another room for a few seconds. Build up the time slowly. Have him in the crate, leave the room for 30 seconds if he does not whine then re-enter the room and praise him along with a treat. If he whines then tell him quiet from where you are do not re-enter the room. Not only should he be quiet but he will also know that you are not far away. After it builds up in time the next step would be to leave him loose in the house and you go outside. If he starts whining then tell him quiet again. This will reassure him that you are there. Build that up to some significant time. The next step would be to leave and go out. take the car around the block and return. Again build the time up to where you can be away slowly. You might want to leave a radio or TV on when you do this. You might also want to have a tape recorder going to record if he barks or whines when your gone.
Also when leaving the house give him something to do such as a kong or two filled with treats. I use the kong ball as it is harder to get treats out of. Begging strips are great if left as large as possible.
Over a period of time you will be able to leave him on his own. It takes weeks to do this but since you do not have school until September you have plenty of time.
For the not liking men part have your dog in the same room as a man or outside. The man should not make eye contact with the dog and not talk to the dog. The man should then throw a treat towards the dog. Slowly decrease the distance between the man and the dog feeding him treats until the dog is at arms length then have the man give the treat by hand to the dog. Don't rush into it and expect the dog to like men after one day, all the above takes time and a lot of patients.