Charles said that he and his family live in the North East. That covers a wide area with a lot of different threats. Annapolis, MD has a lot different risks and threats than Niagara Falls, NY, which is a lot different from Augusta, ME. So the next thing I'd suggest is that they look at their risks and the probabilities.
Several years ago, I developed a tool that allows a person to enter their potential risks and threats, the probability for each to happen, and how big the effect would be if it did happen, then it assigns a numerical priority to preparing for that threat. Unfortunately, I can't find it on my computer. I'll keep looking and put it out here when I do. But Charles should do go ahead and figure out exactly what his personal risk hierarchy is. Once that is done, he can prioritize his preps, based on his budget.
An important thing to remember is that because of disaster commonality, many of his preps will be useful for many of his risks. In fact, if he is 75% prepared for 75% of his risks, he'll be way better off than most other folks, and in pretty good shape for that other 25%. The preps for a winter storm are not that different from those for a late summer hurricane, and not that different from those for losing your job.
I'd also encourage Charles and his family to limit dependence on they system. Grow a garden, harvest rainwater, gain repair skills... In lieu of having a dedicated bug out location, work out a mutual aid agreement with a friend or family member in another location with some prepositioned supplies. Most disasters can be ridden out at home if one is prepared, and even of those ones that actually require bugging out, after most of them, you can return home before two long.
Without more specific information or questions, the only other advice I'd offer Charles is to budget for their preps gradually, paying cash, and eliminating debt. He mentioned that they make a decent living. I'd urge them to live below their means, and build an emergency fund and cash reserves as a part of their preps. He said they'd like to move to a more rural location. If they are perpetually paying down credit cards and car notes and the mortgage on the bigger house in the better location, it will take longer to achieve that. Not having any debt allows an enormous amount of cash to build up faster than they could imagine, which could allow them to pursue their dreams way earlier than they thought.
I wish good luck to Charles and his family, and thanks for the email!
If any of you have any questions or post suggestions, please email them to me.