TimeSharing Today | Jul / Aug, 2026
came the very first family in a newly developed tract housing neighborhood.
She later attended an all-girls Catholic high school after her father spotted a boy kissing a student outside the local public high school. After graduation, she attended California junior colleges before continuing at California State University, Fullerton, where she became part of one of the school’ s earliest graduating classes.
From an early age, Gayle knew she wanted to become a teacher.
Military Life and Constant Change
During her senior year of college, Gayle met her future husband, William O’ Malley. Shortly afterward, William was drafted into the military, launching the couple into a life that would span decades of service, travel, and relocation.
William began his military career as a private before eventually rising to the rank of lieutenant colonel. At one point, the military selected him for a newly created Foreign Area Officer program designed to develop specialists in strategic regions of the world.
“ They asked him in the middle of the night if he wanted Russian or Chinese,” Gayle said with a laugh.“ I told him Russian sounded easier.”
William ultimately became a Russian specialist for the military, leading the family to assignments throughout the United States, Germany, Scotland, Washington,
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D. C., and Moscow-related operations. During their 26 years in the military, the family moved 16 times.
Despite the challenges, Gayle continued teaching while raising three children— Kathleen, Brian, and Sean.
Discovering Timeshare Ownership The O’ Malley family first encountered
OWNERSHIP & TRAVEL
timesharing while living in Washington, D. C. during the early 1980s. At the time, they had three teenagers and had outgrown their small camping trailer.
The concept sounded appealing, although unfamiliar.
After attending a presentation, the family received an incentive stay at Vistana Resort near Disney World in Florida. The location proved irresistible for a family with teenagers eager to experience Disney attractions.
“ When we saw Vistana, it was beautiful,” Gayle said.“ We bought right then.”
That first purchase occurred in 1984 and remains part of Gayle’ s portfolio today. Unlike many owners who later converted to points systems, Gayle retained her original Vistana ownership as a fixed week because converting would not have provided enough points to recreate the same vacation value.
Over time, the family expanded into additional ownership interests in Marriott, WorldMark, Shell Vacations Club, and Welk Resorts, which later became part of Hyatt Vacation Club.
Watching the Industry Evolve
Gayle’ s experience mirrors the broader evolution of the timeshare industry itself. In the early years, ownership typically meant a single fixed week at the same
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