having just started using e cigs after over 25 years of heavy smoking, the first thing your going to have to do is know if he is truly ready to quit. if he's not, don't waste your money or time. the next question is, do you smoke your self and do you vape? do you know anyone personally that does it? if not convincing an older person (over 40) that vaping is the wave of the future is probably going to be an up hill battle, a success story from a close friend that can help with the learning curve is very important.
i did not have anyone to turn to other than this message board and the google, i am also an adventurous person so switching to e cigs for me was as easy as going out and doing it, i also had a high desire to quit (i felt like crap all the time)
be prepared for disappointment if they are a stubborn personality, my sister in law lives in our house, still chain smokes, and refuses to even entertain the thought of using the e cigg even though both my chick and her girlfriend both got on board when i started, another thing to remember that "e cigs are worse than real smokes" "they have anti freeze in them" "i dont like chemicals" you name the excuse ive heard it, the nail ive used over and over with success is to take a giant drag off of a real smoke then blow it through a paper towel, and show them the nasty goop that comes out, then take an even bigger vape and blow it through the towel and show them the nothing, that more than anything convinced at least two naysayers that its got to be better than real smokes.
that being said, i started out with a blue starter kit and the assortment of flavors, i know now that its only a gate way device, but its a place to start, you might also want to pick up an eGo starter kit to have on hand, but that is a little forward thinking because of the "fiddling factor" that is involved. i smoked so much i was constantly killing the blues. also remind the person that your trying to help that you can still smoke while using the e cig, unlike the gum or the patches (although probably not advisable, but who ever listens to drs anyway)