Can't see the pics from here (damn firewall, attached/uploaded images from the forum itself come through OK though), but paint peeling off of a surface is usually:
- prep problem with a dirty substrate/layer;
- or moisture underneath causing the paint to peel off;
- or poor paint (bad batch of paint) or painting (improper temperatures, improper materials/solvents, improper application, etc).
http://www.sherwin-williams.com/do_...ques/painting_problem_solver/peeling/Peeling/
http://www.sherwin-williams.com/do_..._solver/peeling/Peeling_DueToMoisture_Inside/
http://www.sherwin-williams.com/do_...s/painting_problem_solver/peeling/Blistering/
And their general 'peeling paint' page:
http://www.sherwin-williams.com/do_it_yourself/painting_techniques/painting_problem_solver/peeling/
For most paints (barring some industrial-type coatings or maybe epoxy-type coatings) there is generally no problem or incompatability with putting latex/acrylic paint over or under oil-based paint once the paint films are fully cured and dried IF the surfaces and films are in good condition (clean, dry, good adhesion underneath, etc). Although the 'general' rule is latex/acrylic top-coat with oil-based primer/undercoat because of the difference in expansion/contraction (acrylic expands/contracts more than oil, generally, so the more 'flexible' paint film on TOP is usually OK ,whereas a harder less flexible oil-based paint film on top of a softer more flexible acrylic paint film underneath can lead to problems). In general.
re: moisture and brick and vapor barriers
As mentioned, brick (and masonry in general) is porous and lets moisture through pretty well. If the back of the outside brick is right up against the outside sheathing (the "1/2"ish thick black particle-looking compressed fiberboard of sorts", which sounds a bit like a type of Homasote board/sheathing ), then you may have BIG problems as moisture will have soaked the sheathing (there is SUPPOSED to be an air gap/space between the sheathing and the back of the brick/masonry just for that reason of keeping water from touching/soaking right into the sheathing). Which may have turned it all black from mold. Which is a BIG (and finally recognized) health problem.
I measured - the gap between the black layer and the brick is 4".
If there is a large-scale black mold problem, the semi-good news -may- be that homeowners insurance policy MAY cover the costs to fix the problem. Check to see if there is mold and check to see if your policy covers it.
Just leaving the mold in the walls is NOT an option, as the spores spread and get air-borne. Moldy drywall has to be removed, and moldy framing (joists, bottom plate, rafters, sheathing, whatever) has to be treated to kill and/or encapsulate mold. If the wood is not rotten as well, in which case the wooded items have to be removed and replaced.
Don't ignore possible black mold problems. The only real way to tell is to open the wall up and look. Doesn't necessarily have to be removing the WHOLE wall, at least for the first look-see.
If the mortar on the brickwork is cracked or crumbling or otherwise damaged, then you may have to tuck-point the exterior. That involves removing 'bad' mortar and removing enough 'good' mortar to allow you to go back and repack and retool (smooth and shape) the mortar joint(s).
I've already been planning to do this. I closed up the cat door on that wall a few weeks ago (replaced about 14 bricks) so that's when I took note of the condition of the wall, particularly the mortar. Many of the holes are located in the vertical joints of the wall. Looks like the mortar got soft and crumbled and washed away with rain.
re: pulling nailed drywall down
Usually not possible. You can't (usually) just pull the drywall sheet intact off the framing, as unless the fasteners are SOOOOO bad/gone/poor as to be non-existent, the drywall will break/crack/etc when you go to pull it off. And you (usually) can't get a nail-puller (cat's paw, Wonder-Bar, etc) into the surface to pull the nails without (usually) wrecking the surface of the drywall from the digging and prying. If you can even FIND all the nails. Same for drywall screws, unless you have LOTS of patience and some skill/luck at popping a screwdriver tip exactly into the (buried under paint and paper/fiberglass tape and joint compound) hidden screw recess. One of those theoretically possible tasks that really doesn't happen in the real world.
Yeah, I figured that wouldn't be easy. Again when I worked on that cat door area I pulled off the torn up drywall around that framed section so I could see the studs. I was disappointed to see the nails holding the drywall in. The pieces had to be broken off then the nails removed on their own.
I don't know, I don't think it's going to be a simple pull a sheet down and put it back. I've looked at drywall prices a little bit already when writing up my reno plan. I was figuring $300 for materials.
What I don't want to do is pull the wall down and redo it only to tear it down again because we need to get to the ceiling a year down the line. (How do you do juts the ceiling only when the ceiling drywall has to be installed first before walls?)
I'm not convinced there's mold in there. But then again I just saw what our 1985 Trane air handler looked like
There wasn't any mold on the drywall which was directly around the cat door, and I know moisture was getting in there.
I can hear it now, "Sweetie, we already talked about this". 
btw, are you the holster-maker from WeldingWeb? If so, hi. If not, hi too.
