This post was written by Khaleef Crumbley from Fat Guy, Skinny Wallet as part of the Yakezie blog swap.

As part of this blog swap we were asked to write about our biggest financial mistake and also what we learned from it. Well, our biggest financial mistake occurred about seven years and two weeks ago.

It was a dark and stormy night… Actually, it was a beautiful sunny day in Mexico while my wife and I were on our honeymoon. My wife and I were extremely happy with the frugal decisions and the help that we received that allowed us to keep our wedding costs under $5,500. We also received two weeks from my mother’s timeshare and we were able to stay at two different resorts (it was really three, but I will get into that a little later) for free!

A Great Start

While we were in Mexico, we were approached each day by several people who were trying to get us to sit in on timeshare presentations in order to get free items or, in some cases, cash. We sat in on several during our stay and were able to take part in a couple of tourist activities for free.

The first resort in which we stayed was pretty much our idea of perfection; while the second resort was a lot like a huge hotel that was in a fairly remote area. It was while we were at the second resort that we encountered our final timeshare sales presentation.

Going Downhill In A Hurry

The guy who tried to sell us on the timeshare was probably one of the worst salesman that we have ever come across. Even with that, the numbers and the options seemed so much better than all the other presentations that we had been to. For some reason, as we continued to look over the options that were presented, we thought that it actually made sense. 😳

I don’t remember our exact thought process as we talked to this gentleman – I believe his name was Jimmy – but from what I recall, a conversation with him was not enough to push us over the edge. That’s when he brought in the big guns!

By “big guns”, I mean a woman named Grace (or Gracie, I’m not sure). From what I remember she was an attractive, well-dressed, articulate, funny, and seemingly intelligent woman. My wife and I immediately took to her personality and by the time we finished talking to her, we were convinced that we would be almost foolish to leave this deal on the table.

There were a few things that factored into our decision: We were convinced by the fact that we could exchange our timeshare for one closer to us (to avoid the cost of a flight out to Mexico), we could sell our week if we weren’t going to take a vacation that year (we were told how huge the market was for individual timeshare weeks), and the two exchange companies that we became members of both had deals to give you free weeks (or at least weeks at a tremendous discount) if you are willing to book them within a month or two of the time of travel.

Also, one of the exchange companies gives 2 free weeks per year to all members (these are separate from those last-minute deals I just mentioned)!

Every time we thought of an objection as to why it would not work for us, Grace was able to come back with a provision in the contract or a feature of the timeshare itself that would allow us to easily overcome that objection. Needless to say, we purchased a timeshare a little over seven years ago and that purchase has haunted us ever since.

The Big Lesson

I think the biggest lesson that I learned from this is that I need to be able to conduct my own research before entering into any deal. Since the economy was doing so well in 2006, I’m sure that the timeshare market was booming and that people who owned them were able to make money just by selling their weeks (something that we were assured of). However, I should have made myself familiar with how the market normally responds in the middle of a recession (since I expected one to happen in a few years).

We also should’ve looked at just how long it takes for someone to see a sale once they put a week on the market, and also how much, if any, they have to reduce their asking price.

We also should have talked to people who currently owned timeshares to find out if they had experienced significant increases in the maintenance fee since they signed the original contract. This is something that has plagued us greatly – the first year’s maintenance fee was under $500 and seven years later it is now up to about $750! I guess the one good thing is that we only pay this fee once every two years.

It would’ve also made sense to research what the average exchange fee is for moving a week from the home resort to another within the system. Another consideration would have been how often we plan to use the timeshare and what the cost of our lodging would be without it.

Here is the full financial blow: the timeshare cost about $5,000, an amount which we had to finance and a very high interest rate. After making payments for less than a year we decided it will be better to use a zero percent offer from one of our credit cards to pay off the balance. On top of that, this year is the fourth year in which we had to pay a maintenance fee. In 2007 this fee was less than $500 and it has gone up each year to be about 750 this year…who knows what it will look like in 2015.

Our Lesson Applied

Hopefully by now you can see the importance of researching every financial deal before you sign on the dotted line. Had we considered any of the things which I listed above, I’m sure that we would not have taken the offer. I guess the one good thing out of it is that after we signed the contract they allowed us to move from the mediocre resort into their resort (which was as amazing as a first resort)!

My wife and I conducted an abnormal amount of research one year later when it came to purchasing a car. Every time we began to talk about finances in the dealership I whipped out my laptop and was able to examine every detail of the deal using my spreadsheets. We have definitely learned our lesson from the timeshare incident, and every time we have to drain our bank account to pay one of these maintenance fees, or look online and see the tens of thousands of timeshare weeks that have filled the market, we feel the pain of our mistake.

So if you don’t remember anything else from this little tale, please promise me (and yourself) that you will always perform the necessary research before entering into any financial arrangement! There are also reputable companies that can help you do a timeshare exit to remove yourself from your timeshare agreement and stop your maintenance fees.


  1. Oh man, sorry to hear that. Every timeshare owner has the same story to tell. I’ve been to a timeshare sale event once and escaped without buying anything. I’m never going to one again. Thanks for the reminder.

    • @Joe – I’ve been to a sale as well, and those sales people really are pushy. Thankfully, our “tour” went sort of south and we were very disgruntled by the end of it – the timeshare gave us our “free” items, but really didn’t try to hit us up on purchasing anything.

    • You know, the sad thing is that we kept telling ourselves that we wouldn’t buy anything, and we felt great for turning down the other presentations. We must have let our guard down and now we are still paying for it!

  2. @Khaleef – Two sets of our parents own time shares. One set I think is regretting their purchase – it wasn’t at all what they thought it would be. The other absolutely loves it, but they take advantage of a lot of the free weeks and give them to relatives when they can’t use them. I think timeshares only work for frequent travelers and if the associated timeshare can be swapped at many locations. Thanks for the great post!

    • My parents own 2 and I loved the fact that they were able to give away weeks to relatives (especially when we got 2 of them for our honeymoon), but as you said, you have to be a frequent traveler and have flexibility in order to make it work. I’m not saying they are terrible, but definitely not something we should have done as a couple who was already in debt 🙁

      Still paying for this one…

  3. The timeshare industry wants educated owners, which is why the American Resort Development Association (ARDA)—the trade association that represents the timeshare industry—launched our consumer website, If you understand the product offerings and that the value of timeshare comes from use, then you become one of the 83% of satisfied timeshare owners. An educated owner prior to going on tour ends up a happy owner!

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