I am considering buying a power generator. Is there a scheduled second US power outage to take place where I am during the winter, which would be more serious in terms of survival?

Unfortunately, this is likely to happen. So you are in the best possible situation if you have access to a power generator. You can try to tough it out, but have that as a backstop. A generator of the kind you have been looking at will be quite adequate to the task of taking the edge off the discomfort, and that is basically most important here, to get through it unscathed, even with some inconvenience and discomfort that will be unavoidable. Again, this outage will not be intended to be lethal and so might be shorter than the first one, but just to give a further taste of what this can mean when it happens under the worst weather conditions. So again, your decision in how to proceed here with preparations and precautions is up to you. We see the advantages in terms of having a less painful experience and that would be the case in owning such a device.