1) I'm not confident that either the antenna or coax are serviceable at this point. Consider replacing the coax as the next step. (Standard RG-6 or RG-6/U, no need for quad-shield) That allows you to test with your indoor antenna on the roof if you choose. (you may need a 'barrel' connector.)
2) If you still don't see KGO, I'm with John on the recommendation regarding an FM trap. They are inexpensive and there is a real chance you will see KGO as a result.
There is more than enough signal in the air for a set of non amplified rabbit ears to receive an excellent signal from KGO provided there is minimal interference from FM or multipath.
The old roof top antenna is missing elements that will effect it's VHF performance, it's not a viable standard to use in judging signal conditions.
An HBU-33 is more than enough antenna based on gain, it's directivity may be needed though. By trying the two steps I've suggested, you can hold off spending money on a new antenna until you have more conclusive information to work with.
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If the well is dry and you don't see rain on the horizon, you'll need to dig the hole deeper. (If the antenna can't get the job done, an amp won't fix it.)
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