Insulating Walls with electrical devices

[rob1315]

Great forum...I'm definitely putting this in my favorites.

I've got a couple of questions about insulation if someone could indulge me. I have an old garage which has been enclosed and is lacking any insulation in the south and west facing walls (extremely bad news in south Louisiana from June-September). I am about to have vinyl siding installed on the whole house, and I have decided that now is the time to install insulation in those two walls. Rather than ripping out the sheetrock on the inside of the house, since the old siding is cheap and rotting fiberboard, I am going to go in the opposite direction and rip off the old siding. There is tar paper under that, and then air between it and the drywall on the inside of the house. Once I have the insulation in, I am going to put up 7/16" OSB and then the contractor will put the insulated backer board and siding on top of that.

So here are my questions:
1) Should I even bother with a housewrap assuming the insulated backer board is going to be taped?
2) My understanding is that insulation should be cut lengthwise and fit around wiring that runs through studs such that the fiberglass material surrounds the wire. Is that correct?
3) My understanding is that insulation should go behind all outlet boxes with the fiberglass side adjacent to the backside of the box. In other words, I don't have to cut out the insulation behind the box. Is that right?

Also, I have assumed that since my climate is predominatly hot and humid, I should have the vapor barrier (paper side of the insulation) facing the outside of the house and that, in effect, the pink fiberglass side should be directly behind the sheetrock. Please set me right if this is wrong.

Thanks in advance.