You're speaking to Dr. Michael Salkin. Welcome to JustAnswer. I'm currently typing up my reply.
I'm sorry that your question wasn't answered in a timely manner. I'll answer your questions as you presented them...
1) The correct amount of food can be estimated by feeding the recommended amount as posted on the label of the dry food. To be more exact, I can tell you how many kilocalories of food Tom needs daily if you tell me how much he currently weighs.
2) Fresh meat isn't necessary. I'm sure that Tom would like it as a treat, however. A mix of dry and wet food is more palatable but not necessary. He doesn't need additional fat when a balanced commercial food is fed. It has the proper amount of fat, carbohydrates, and protein.
3) Anal glands are vestigial organs (as is the appendix and ear lobes of us) that have no purpose in dogs. Impaction/infection of these glands is common. When this occurs most dogs scoot on their rears, lick their anus, and may express the odiferous exudate more so than usual. You would find the odor of skunk or a metallic odor about his anus.
4) Puppies exhibit exploratory behavior and Labs, in particular, will eat anything that doesn't eat them first. You'll need to puppy proof his home in order to avoid his ingesting things he shouldn't. Excessive pica (ingestion of non-food items) can result from starvation as well.
5) Your father isn't correct. Regular flea prevention and worming is smart - usually monthly. Some flea preventatives also worm your dog; the best are the newest ones available through Tom's vet.
You're welcome. Please respond with further questions or concerns if you wish.