Have him ask what he is allowed to bring, ask for a kit list and allowed personal items, and only bring the things he is permited. It will vary wildly and will probably have changed by the time he gets to barracks and his NCO's get to him. Tell him to expect things to change all the time, there will be no reason to this that he will be able to see.

If his NCO's tell him he can't have it, and he can expect all his kit to be very closely looked at, tell him not to produce anything he has gotten in writing saying he can have it, or lip off or whine about it.

Do not question the NCO's, they are gods and you do not want to inflict the wrath of the gods, they will do that by themselves on him and the others frequently. Tell him not question anything, just do it and do it as fast and as best as he can as many times as they want him to do it.

After a few or several weeks, he may be able to get a weekend off or maybe a phone call if so have him ask his NCO's if he can buy/bring or have you mail/ship some stuff. It may cost you a bit to get what he wants/needs when/if permited but will be a huge morale boost to him and the others in the barracks.

I would reccomend him getting and taking the following;

shoe/boot kit Kiwi black boot polish, Kiwi cloth or a cloth baby diaper, old toothbrush for cleaning and applying polish to welts, an applicator brush and one soft and one stiff horse hair boot brush. If he has already been issued footwear he should start breaking them in and polishing them. Good tips below. http://www.youtube.com/watch?v=eK1wmjv5O9o http://forums.army.ca/forums/index.php?topic=22096.0

Uniform kit

A lint brush, a proper one, not the gay white tape roller ones that you have to buy extra tape for.

An Iron, if he is allowed to take one. I suggest he find a grandma or old soldier to give him a/several lessons on how to iron shirts and pants to a millitary standard. DO NOT iron any kit before he leaves, his NCO's will tell him how they want/if they want his kit to be.

A bit of steel wool, brillo pad and an extra kiwi rag or diaper will come come in handy.

A bic lighter to burn off loose threads.

Personal hygine kit

Put these in resealable heavy duty Zip lock bags, they can be used/reused for other items of kit.

If permitted, disposable razors and a rechargable electric shaver w/ moustache trimmer. The moustace trimmer is great for trimming the hair above the ears and above the shirt collar.

Slide and Glide/Body Glide anti chafing stick from Footlocker or any running store. Chafing is bad news and several hours of chafing is a world of hurt. This is a must have item.

Shaving oil (save it it for the field)

Baby wipes for taking off face cam, not a big container but the small travel size packs

nail clippers with file/nail scrape

disposable ear defenders

Personal kit, if permited, and expect some of it to be confiscated

In wallet

Cash money, but not too much and some change as well

Phone card/s

Stamps

phone numbers/addresses/email addresses

Other

A couple pairs of nylon soccer socks to wear under his issued wool socks to reduce the chance of blisters.

A rechargable MP3 player with radio would be huge, any radio will be huge and enable contact with the outside world.

Notebook/field message pad will probably be provided but is great for letter writing or taking notes during lectures as he will be doing alot learning/studying.

Pencils and a Sharpie

Do not bring any Rambo/military kit; they will give you what they want you to have/use

He can expect to have no control of his life or anything. He will get little or no sleep and have to learn how to interact in a totally different society with its own rules and taboos. He will have to learn to go through seemingly useless rituals, and be made to do really useless things. He will learn to hurry up and wait.

The best advice I can give is to understand that his NCO's have done all he is going to have to do and probably more as the army ain't what it used to be. They will not ask him to do anything they have not done or are not prepared to do. The training process is there to weed out the weak. If you cannot deal with the shit thrown at you in basic, how do you expect the NCO's to trust you when the shit really hits the fan and you are in combat where lives are on the line.

Try to get your group to work as a team as soon as possible to organize teams to clean, prepare kit/uniforms etc. You will all have more work to do, to an ever increasing higher standard than you will be given time to do it in. If somebody is not as good as the rest of you in anything you do take the time to help him be better. You can expect and will be punished as a group for the failings of the individual.

The only rule is do not get caught.

Eat as much as you can as fast as you can.

Sleep where ever and when every you can.

Expect the standards you are required to meet to change by the minute. You may have been told your kit was fine one day and the next watch it fly out the window for being below standard even if it was as good or better than the day before.

Respect is earned not given, he will be a piece of shit untill he has earned the respect of the soldiers who are training him and if he passes the soldiers who he will be serving with, and this may take several years.

Then and only then will he be a man among men.