Nick, that just leads one to wonder why the wide pulse of SS High then?

Which I would submit is the commanded high followed by the code wrapping around back the start of the void loop.
Yes I was wondering about that too, but I assumed it was too large to be called a glitch.
I should point out too that the order of operations in the setup is a bit suspect. Check out what SPI.begin does:
void SPIClass::begin() {
// Set direction register for SCK and MOSI pin.
// MISO pin automatically overrides to INPUT.
// When the SS pin is set as OUTPUT, it can be used as
// a general purpose output port (it doesn't influence
// SPI operations).
pinMode(SCK, OUTPUT);
pinMode(MOSI, OUTPUT);
pinMode(SS, OUTPUT);
digitalWrite(SCK, LOW);
digitalWrite(MOSI, LOW);
digitalWrite(SS, HIGH);
// Warning: if the SS pin ever becomes a LOW INPUT then SPI
// automatically switches to Slave, so the data direction of
// the SS pin MUST be kept as OUTPUT.
SPCR |= _BV(MSTR);
SPCR |= _BV(SPE);
}
So the SPI.begin () overwrites some of the stuff you (maxmike) did before calling it. I can't really explain why SS becomes high during the transfer, except maybe the circuitry itself is responsible?