Now as far as the EMT stuff for your son goes. I know that amount and type of calls vary from area to area. In NYC as EMTs we get a lot of trauma although now I’m doing more medical calls due to paramedic training. Because of that tools will vary a bit. Good stethoscope is a must but let your son choose what he wants. Blood pressure cuff is pretty standard unless you want to get him a set with glow in the dark dials and different cuff sizes. Get him a good duty belt, glove holder and radio/shears holder. Also Benchmade rescue hook is a life saver (I wrote review about it here of ETS). It works better than shears. My belt also has multitool attached and I carry Spyderco Assist in my pocket. I also have emergency repel belt and it came handy during few roof jobs as my personal safety. Our Heroes (FD) respect medical profession very much and would much rather have us doing medical work than trying to play doctors. Also solid boots will save his ankles, feet, knees and back. I saw people also using combat shooting gloves for doing 10 fl carry downs. I personally have a nice set of construction calf skin gloves that suit me just fine. But the most important buy is a portable DVD player so he can watch all the movies in between calls. 

You can’t go wrong with the pelican light. Everyone wants Surefire but at one glimpse at mine they all end up getting M6. Also since Pelican is totally unsuitable to check pupils ARC AA is much better (and your son has a fine taste)

I also carry a small puls/oxygen (pulsox) meter. But I don’t recommend it for the reason that you need to get you vitals perfect without use of any gadgets. Only when you know how to take them with your eyes closed while hanging upside down you can start going for gadgets that make your life easier.