I would not suggest all of it at the same time, he could protest. Here is what I think to be good :
first month, just have him getting his top & bottom brackets and a untight wire, so that he's not really in pain, but everyone see his braces, after three weeks or so, a hard wire tightening.
Second month, have him getting a top expander without pre-notice. At this time, have your ortho friend prescribe him a headgear for 20 hours a day, which he won't wear anyway (; ))
After 8-10 weeks fit a lower expander and two tongue cribs : top and bottom, so that he is really annoyed.
At week 13 (let's say), his ortho will notice he has not been wearing his headgear. Make no comment about it and say she'll adapt his appliances to his progress, and wire it in. Finally, put on a herbst appliance. He'll probably be in pain, but that's what you want, don't you?
Now you can have something like 10 months with 1-2 appointments a month for tightening. Afterwards, wire the HG out, and prescribe a combination headgear-facemask.
So, to sum up
T=0 : brackets and neutral wire
T+3 weeks : awful tightening
T+6 weeks : top expander + HG prescription
T + 9 weeks : bottom expander + two tongue cribs
T+13 weeks : wire in HG + Herbst <<<- For more fun, you can add some ortophonist lessons for more shame
T+15, 18, 20, 23, etc... : Appointment for tightening, he'll ask for removal, say no. + Add 5-6 elastics with complex pattern. Add coil springs for more fun and pain.
T+40 weeks : wire HG out, prescribe facemask + HG + (if you want) neck headgear
T+52 weeks : remove herbst, have him wearing a removable herbst with threat of having fixed herbst put on again
T+60 weeks : remove some devices (I would suggest one tongue crib and the top expander), leave braces, HG, and rubber bands. keep having appointments regularily. feel free to wire HG in again, especially the facemask. He'll believe it's the end, however it wont be ; )
T+ 100 weeks: remove all but braces.
T+ 120 weeks : remove all, have him wearing huge retainers with HG if you like. Don't forget the bound contention wire, which can be as thick as you like.
I'm sure he'll cry