Use a "load" to verify socket terminals are getting actual power that can fire a 300W bulb! A DMM is a high impedance device and will show more than adequate voltage which can sag to nearly zero under load.
Can you please be more specific? I checked the voltage by the transformer while a bulb was in socket. It measured the same as it did when the bulb was not in the socket. Thanks for your help.
The bulb was not illuminated though, correct?
This sounds like a contact issue.
If possible wire up a medium based socket or any household lamp to the transformer and screw that bulb into that socket. The lamp should illuminate if the transformer is working properly.
Tried the bulb again in the hopes that I connected the wires again and now it was a better connection. No luck so I am left with the assessment that the pool light fixture went bad. Those things run about $200 on Amazon. Sucks 🙁 Looks like we will not have a pool light for a while. Thanks for your help.