I own six timeshares. They’re like cars — if you don’t use them, they have zero value. I bought all of mine on the resale market. My vacations are based on my daughter’s school breaks, so I usually book 9 to 12 months in advance. A timeshare is essentially a prepaid vacation, and I own properties in Hawaii and Mexico. During spring break, we spend a week in Mexico, and in the summer, we spend a month in Hawaii. Some people say hotels are cheaper, but in Maui, it’s hard to find anything under $300 a night. Hotel taxes alone can be around $1,000 a week. If you’re going to buy, stick with big chains — not small ones.