Finally got 2 openGL views working in a single window. Cocoa seems to be very fussy about the order and timing of some of the calls to its helper context class. Here is my call flow

Here is my init

- (id)initWithFrame: (NSRect)frame
{
self = [super initWithFrame: frame];
if (self)
{
doDraw = NO;
doInit = YES;

NSOpenGLPixelFormatAttribute attrs[] = {
NSOpenGLPFADoubleBuffer,
NSOpenGLPFADepthSize, 32,
0 };
m_PixelFormat = [[NSOpenGLPixelFormat alloc] initWithAttributes: attrs];
/* Check if initWithAttributes succeeded. */
if( m_PixelFormat == nil )
{
/* initWithAttributes failed. Try to alloc/init with a different list of attributes. */
NSLog(@"ERROR: Pixel Formal NOT supported");
}

m_Context = [[NSOpenGLContext alloc] initWithFormat:m_PixelFormat shareContext:nil];
if( m_Context == nil )
{
/* initWithAttributes failed. Try to alloc/init with a different list of attributes. */
NSLog(@"ERROR: GL Context not created");
} else
{
[m_Context makeCurrentContext];
[m_Context setView:self];
}
}
return self;
}


and here is the drawRect

- (void)drawRect:(NSRect)rect
{
[m_Context makeCurrentContext];
[m_Context setView:self];

if( [self inLiveResize] )
{
// Not sure yet :-)
doDraw = YES;
}

// Only draw if timer fires
if (doDraw)
{
doDraw = NO;

[self draw];
[m_Context flushBuffer];
}
}


I use a Timer to set the doDraw BOOL as not to force a drawRect. I also still need to read more about inLiveResize to see if I can still update the engine or not.

Here I setup the timer and a default scene, this function is called in applicationDidFinishLaunching, as you can see my engine is C++ and I'm finding that mixing ObjC and C++ is working very well.

-(void)startup
{
NSLog(@"startup: Init game...");

[m_Context makeCurrentContext];
[m_Context clearDrawable];
[m_Context setView:self];

// cpp code: Create our demoapp
// This sets up the engine and keeps the custom view clean
default_scene = new DefaultScene();
if( default_scene )
{
// cpp code: init our app, needs active GL context
default_scene->InitEngine( 60.0 );
default_scene->InitGame();
}
// Add engine update timer
m_Timer = [NSTimer scheduledTimerWithTimeInterval:1.0/60.0
target:self selector:@selector(triggerGameDraw:)
userInfo:nil repeats:YES];

}


I'm posting this in the hope it will help someone else having issues with Cocoa/OpenGL.