No heat is probably the biggest problem of a prolonged power outage. It was after an outage of a couple of days without power in the winter that I broke down and had a transfer switch installed so I can cycle through running the refrigerator, furnace, sump pump, and some lights/outlets. I also always keep a kerosene heater in operating condition to run in the basement. Next step is a bigger generator so I can run them all simultaneously, along with at least one window AC unit. With more and more days/nights with dew points in the 70s here, however, AC is moving from nice to have to a week without AC in July and August would be miserable.
Haven't had to use the transfer switch yet. I'm thinking tomorrow may be the first time if landfall is along the RI coast.