Here are a few of the reasons I bought a timeshare at Simpson Bay Resort and m glad I did. First, it forces me to take a vacation. For us workaholics who are also frugal, it is a way to make us take a vacation when we might otherwise just stay at home and work. The renting he cost of the unit and the cost of maintenance fees when amortized over the years works out to be a bit less than renting the comparable unit. The main advantage that we're guaranteed the same unit with a spectacular view. When renting, especially now that there are fewer units after Irma, you may have difficulty finds the right unit during High Season. We like knowing that we have the same unit every year, knowing exactly what's in it and where we'll be. It was never an "investment" and was not ever going to be.