1. Acoustic drums are way better IMO, maybe starting out it wont bother him but every time I try to play electronics I can't open the high hats the way I want and the snare and cymbal chokes seem so artificial sounding, I don't even mind the rubber pads as much as just the lack of expression, but they are fun to play with all the sounds and practice at 2AM, if you have a mixer and headphone amp/splitter you can even have every one plug in and wear headphones and have a silent jam session.
I'm aware you have already decided on a electronic kit and I'm not telling you not to get one, I'm just stating my opinion, I have had an acoustic kit for like 8 years and as long as I'm not bashing the crap out of it when people are sleeping or on the phone my parents never cared.
2. I agree with the recommendations get a Yamaha or Alesis, Roland wants way to much money and I would only consider them if there is a certain feature you want and are willing to pay for.
3. About the headphones, I think you will find using him and yourself using the monitors at lower volumes more than head phones but headphones are still a good idea. About his hearing, your just going to have to tell him to not turn them up to loud, I wouldn't worry to much, why would he go deaf in the first place? He probably listens to music louder than the will he drums.
I don't like the 280HD's not enough bass and they are going to get really hot really fast drumming and have a very hard clamping force. The DT770's Pro 80ohm and the 770M drum monitors are popular with acoustic kit players because they have a lot of sound isolation, however I would say they are better than the 280's having more bass and being more comfortable with velour pads but still having a strong clamping force to stay on your head.
I'd suggest Ultrasone HFI580's, Creative (CAL!), DT770's (getting hard to find) or even something like the V-Moda M80's or LP2's would work.
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Well your original question was about headphones but I would suggest you to buy him Yamaha DTXpress IV. They are pretty decent drums and not so expensive. Their pads are much better responding compared to Roland's in same price range.
Also electronic drums do not mean a sound free environment. His drumsticks will still make some fine amount of noise. Also, he will insist on an acoustic one in a year or two so be prepared
I agree you might wanna pick out a nice room in the basement and install some sound deadening.
