The problem--too many different health insurance transitions

Johnny was born while his father, Sam, was away in the service, so his first health insurance was through Tricare (1). Sam came home and went to college, obtaining student health insurance (2) that covered Johnny as a dependent. Sam graduated and went to work for a large corporation, obtaining employer-sponsored health insurance (3) that covered Johnny. A year later the corporation changed insurance companies (4). Sam left the corporation and started his own business, obtaining small business health insurance (5). Sam died in an auto accident, and Johnny’s mother, Jane, was left in debt. She had to sell their house and move in with her mother, and Johnny was now covered by Medicaid (6). After a few years, Jane was able to go to work and get benefits (7).
Johnny graduated from high school and enlisted in the service, where his health care was provided for in military facilities (8). His unit was sent into combat, and he was injured. His body recovered, but he was left with a post-traumatic stress disorder and discharged medically with a 20% service-connected disability, for which he sought treatment at a VA Medical Center (9). He found work and started college, where he enrolled in the student health insurance (10). One night he had too much to drink and lost control of his car, suffering a broken leg. His hospital treatment was billed to his auto insurance (11). He graduated from college and went to work in a bank as a loan officer. After a waiting period he became covered by its medical insurance plan (12). He met, fell in love with, and married the female letter carrier who brought mail to the bank, and he now had secondary coverage through her insurance (13).
However, one day a disgruntled client whose loan application Johnny had turned down returned with a gun and fired wildly, striking Johnny in the shoulder. He was taken to the hospital and treated, the costs being billed to the bank’s workers compensation carrier (14). His injury wasn’t too bad, but he decided he didn’t want to work for the bank any more. He went to the state Vocational Rehabilitation department for help in re-training to be a real estate salesman. His PTSD, which had been under control, had flared up, but the VA wouldn’t treat him because the latest trauma wasn’t service-related, so his treatment was paid for by VR (15).
Johnny finally found his niche and did well in real estate. He started with a large agency and obtained coverage thru its health insurance (16), but he did so well he left and started his own agency, purchasing a new policy for it (17). He and his wife traveled a lot, and once while in Mexico he came down with Montezuma’s revenge; his emergency room visit was covered by his traveler’s insurance policy (18). When he turned 65 he went on Medicare (19) and purchased a supplemental policy (20) to cover its gaps.