Electronic – MSP430G2101 WDT not triggering

My suggestion would be get rid of the delay function and use the built in if you are using IAR or CCS."__delay_cycles (cycles);" using the built ins, will give you more predicable results and better timing. You could probably just replace your delay for the built in, to get closer to the results you are looking for.

personally I would go about the whole thing using interrupts and timers to pull the whole thing off and use the peripherals that the msp430 has. I would suggest using the WDT as an interval timer, doing this would leave the other timer for your motor control. p1.3 is used as the wake up pin and p1.0 is the led pin.

example code

volatile int counter;
void main(void) {
    WDTCTL = WDTPW + WDTHOLD;                 // Stop watchdog timer
    P1DIR = 0x01;                             // P1.0 output, else input
    P1OUT =  BIT3;                            // P1.3 set, else reset
    P1REN |= BIT3;                            // P1.3 pullup
    P1IE |= BIT3;                             // P1.3 interrupt enabled
    P1IES |= BIT3;                            // P1.3 Hi/lo edge
    P1IFG &= ~BIT3;                           // P1.3 IFG cleared
    _BIS_SR(GIE);
}
// Port 1 interrupt service routine
#pragma vector=PORT1_VECTOR
__interrupt void Port_1(void)
{
    WDTCTL = WDT_MDLY_64; //enables intervals of 64mS
    IE1 |= WDTIE;  // set WDT interrupt
}
#pragma vector=WDT_VECTOR
__interrupt void watchdog_timer (void)
{
    ++counter;
    P1OUT |= BIT0;
    if (counter == 245) {  //245 x 64mS = 15.6 seconds
        P1OUT &= ~BIT0;
        WDTCTL = WDTPW + WDTHOLD; 
    }
}

Not complete nor has this code been tested, but it should turn the led on for 15 seconds every time the P1.3 button is pushed.

Set VCore() is a function that sets the core voltage regarding to the clock frequency. I am quite sure it looks for some feedback from the hardware to continue. Such as a bit that is set in a register when the voltage is stable. The simulator may not simulate this behavior and the program get stuck in an infinite loop, waiting on a flag that will never get the correct state. If you want to simulate this code, you can safely comment the vcore() line. It won't have any effect on the simulated result. Or, if you want to be cleaner, you could perform conditional compilation such as:

void main( void )
{  
    // Stop watchdog timer to prevent time out reset 
    WDTCTL = WDTPW + WDTHOLD; 

#ifdef SIMULATOR
    // Increase PMMCOREV level to 2 for proper radio operation
    SetVCore(2);
#endif                               

    ResetRadioCore();
    InitButtonLeds();
    InitTimer(); 
    ....

And then define SIMULATOR in you IDE when the code has to be simulated.

I am also sure that the program hangs on the initRadio for the same reason. It inits the RF part, but the simulator doesn't simulate it correctly and your code is waiting somewhere an answer that will never occur.