Screwing the Timeshare Scammers: How we stayed in Maui for pennies.
Timeshares are known worldwide as a purchase so poor, they must pay you $100 or more just to hear the pitch. Horror stories abound of being held virtual prisoner by aggressive salespeople, or even worse the overpaid prices of anyone dumb enough to buy a retail timeshare.
We were dumb enough to attend a timeshare pitch in return for a discounted vacation a few years back. It was a very unpleasant two hours, made even more uncomfortable by the complete a**hole of a salesperson. But it did make me think – is there any way to truly take advantage of this blood-leech industry? And Virginia… it’s not simple… but there is.

These posts will tell the story of just how we turned a hideous two hour sales pitch into a view two bedroom, two full bath, and two kitchen condo on the Maui shore in a top hotel brand. We’ll explain each step in the odossey as we progress through the steps to screwing the timeshare scammers.
Rule #1: Never Buy a New “Car”:
So, most people agonize over new versus used cars. It has always been a dilemma for us whether to save the money on a used car versus the repair risk. Guess what the timeshare salesperson doesn’t want you to know? There is a very active market for “used timeshares”. But the timeshare salespeople definitely know about this market — because they have devised their own protection. There are certain “priveleges” that transfer only for new, versus resale timeshares. These are typically “premium trading” and “points systems” with major hotels. Now the timeshare salesperson needs to speak out of both sides of their mouth: You have “great resale” for your “timeshare investment”, but don’t buy someone else’s resale as you’ll get “much less”. Hmmmm….
Now you might wonder the ratio of a used timeshare, versus a new timeshare. It is STUNNING. For the timeshare we viewed, the approximate retail cost was over $15,000. We easily bought the same timeshare on the resale market for $3,000, and have now –in the difficult economy — seen it for under $1,000. Now why are people paying $15,000 right now today – for something they can’t sell the next day for $0.25 on the dollar? That’s a great question. I believe there are two reasons:
1.) Resale timeshare information is not always easy to find, and many timeshare buyers are not sophisticated computer users.
2.) The timeshare salesperson will make it very easy to buy from them (financing, etc.) – plus the “aura” of your tour and vacation. The resale market is depersonalized, and business-like.
3.) They haven’t found Redweek.com (no this is NOT a promo) – it is a sincere recommendation. Redweek is a virtual Wall Street Journal for the “market” price of resale timeshare deeds; buying just one week rental for one year; and even trading your timeshare for a minimal fee.
Our next posts will discuss the type of timeshare you want to buy, and AVOID — and your next steps to trading to paradise for pennies. Here’s a hint – the San Francisco timeshares are not the best location.
