Should I buy a timeshare? From hidden fees to the difficulty of resale, Wesley Financial Group explains why buying a timeshare might not be a great investment. At first, these properties may seem like a good option. However, the allure starts to fade when you encounter its drawbacks, which include high maintenance fees, upfront costs, and the difficulty of reselling in a saturated market. Before committing to such a significant financial decision, it’s important to weigh these factors carefully.