What follows is a testimonial from my experience.
The Beginning
In 2008, I had to make a trip to Norfolk for work. I couldn’t find a good hotel near Norfolk in my per diem range, so I expanded my search to Virginia Beach, 20 miles away. I found the Barclay Towers, and it was a suite within my per diem for hotels. Then I got the brilliant idea to take my then wife and children along with me since I had a suite. I figured they could enjoy the beach while I was stuck in meetings all day.
The concierge at Barclay Towers was friendly and helpful. Near the end of the week he invited us to a presentation with a “free breakfast.” He wasn’t pushy; he was just doing the job the system required.
The first thing you should know about timeshares is the free breakfast is usually not at a first-rate diner.
At the presentation, they gave us the spiel on owning a week at a resort and how we could exchange our week to go other places. They try to sell you on golf resorts. I don’t play golf, and at the time our family liked to spend time in Lancaster, PA, and there were no resorts available there.
My ex-wife managed the finances at the time, and when they found us a January week at a resort a block away from the beach for about $180 a month, she was eager to take it. She said we could afford it. We signed. The timeshare company in Virginia Beach at the time was Gold Key Resorts. I never had a problem with Gold Key.
Usage
We never used the January week. You get a membership in Interval International and “exchange” your week, then you can book a week somewhere else. Around Memorial Day 2009, we took a week in Williamsburg, VA. It was a nice week.
Other Resorts
Some resorts will also invite you to a sales pitch, and the one in Williamsburg was no different. They try to get you to buy a week at their resort. Timeshare people do not care if you already own a timeshare. They’ll put you through a multi-hour, high-pressure pitch. I don’t recall the experience with Gold Key Resorts being as high pressure, but I’ve been sucked into three presentations at the Williamsburg resorts and they are all the same. After three hours with the original salesperson, if you refuse, you go through a couple more steps, with each person progressively more disappointed with you until you get to the final boss who is personally angry with you while handing you the “free” gift you agreed to accept.
Most of them don’t care if you don’t have money. They don’t care if you’re paying child support. They don’t care if you can’t afford to even use the resort. They all give you the same merciless, emotionless blank stare, like, “What the Hell is wrong with you? All our other customers are walking around with hundreds of thousands of dollars looking for their fourth or tenth timeshare. Just buy this thing!”
These reps weren’t mustache-twirling villains; they were executing a script designed to override customer resistance.
But not all resorts do this. I exchanged at two resorts in the Outer Banks and one in Virginia Beach and did not get sucked into a sales presentation.
The Upgrade
I got divorced in 2013. I kept the timeshare in the divorce because I would have had to give my ex-wife the money to pay for it anyway. Maybe if I were more rational, I should have left her with the baggage, but who is rational during a divorce? I figured I could use it. The week I exchanged for in Virginia Beach was during the divorce while I was trying to decompress and process.
I got remarried in 2014. Around that time, Gold Key Resorts invited us to a presentation in our area at a local hotel. We upgraded to a September week at the same resort. It was about $279 a month. This made sense to us since our anniversary is in September, so we figured we could spend a week in VA Beach every year for our anniversary.
In 2017, we executed that plan. In the meantime, Gold Key sold out or was taken over by Diamond Resorts. During check-in at Turtle Cay, we were invited to a presentation that was supposed to explain some new member benefits we had under Diamond. It sounded like a nice thing. It wasn’t.
The change from Gold Key Resorts to Diamond Resorts altered the incentives of the system. Gold Key had been stable and predictable. Diamond, on the other hand, ran a completely different business model—one built around upgrades, pressure, and point conversions.
The shift felt like crossing a border into a different world: one where the product no longer mattered, only the revenue extraction did.
The Pitch
Diamond used some “points” system that still doesn’t make sense to me. You no longer own a week at a resort; you own points every year that you can use for travel, or even to buy luxury merchandise.
Bear in mind, we were happy with our September week. But according to the sales pitch, most members were converting to points, which would leave the few holdovers responsible for the entire maintenance payment at the resort. They told us our maintenance fee would go from about $700 a year to multiple thousands. They had my wife so scared she was in tears.
They would not leave us alone. We smoked at the time, so every time we took a smoke break, one of the sales team accompanied us. At one point I had to run back to the room to get something, and my wife had to remain there. Sure, they were polite about it, but they would not give us time to talk between ourselves or process things.
When they finally broke our resistance and convinced us this was the “wave of the future,” the financial shenanigans started. For part of a down payment, I had to apply for a Barclay Card with a very high interest rate. Fortunately, Barclay only gave me a $2,500 limit. Our lawyer (more on that later) told me some people ended up with $25,000 on the high-interest Barclay Card. Diamond used them to limit the amount of money they had to finance.
We also had to put down several hundred dollars out of money I had saved for our trip, which limited our plans for the rest of the week. Then we had to finance the rest.
But, oh, wait! We were also past some deadline, so we had to write up an emotional appeal to Diamond Resorts begging for mercy and asking to join their “wave of the future.” I perceived this as more of a dominance or humiliation ritual than a business process.
After at least four hours, we were finally done and walked out with our documents.
But Wait, There’s More
They offered us a long weekend at our choice of resorts where someone would “explain how to get the most out of our membership.” This is timeshare code for “We want more money.”
At this presentation, they told us we bought in at the lowest point level and that wasn’t enough points to do anything. We would have to buy more points.
I tried explaining to the woman that one-third of my net pay went to child support and with the $450 payment for the points, we couldn’t even afford to use the resort. I got the same blank stare. At one point, I even asked her, “Does your average customer walk around with $300,000 in their pocket just looking to buy more points?” She said, “Yes.” I have no idea if she was lying or not.
I couldn’t afford more points, and they weren’t willing to let me out of the office without buying something. Finally, another divorced dad in the office cooked up some scheme to sell us a “right to buy more points” at a certain level. I should have walked out. Why are we conditioned to be polite to people even when they’re essentially predators?
These presentations wear you down. The tone gets more aggressive the longer you resist, and you can feel the room closing in around you. It’s psychologically exhausting by design.
We finally got out of there. They gave us a “gift” of two Android tablets pre-loaded with Diamond content and a couple gift cards. Those tablets were already obsolete in 2017. We gave them to the boys, who broke one. I think I still have one in my office somewhere. I should remember that while I’m decluttering.
Lawyer
That’s enough background. Now for the more technical parts—and the things you need to know.
Yes, there are lawyers who specialize in helping you get out of a timeshare. I don’t remember how, but I came across the Aaronson Law Group. I got the free consultation. I don’t know their prices now, but in 2018/2019, it was $5,000 on the front end and $1,500 on the back end. That was a huge chunk for my finances at the time. I took a loan from my retirement plan to pay it.
The process took a long time. I kept paying the bill because I always pay my bills, until the lawyer advised me to stop paying because Diamond Resorts wouldn’t respond to them. I ordered a stop payment from my credit union.
That was in the middle of COVID, and we ended up in limbo for several years, but we were under the protection of a lawyer, so Diamond could not reach out to us or attack our credit rating. They did report the debt, and that came up a couple of times on my clearance over the years. I just had to provide a letter from the lawyer. The COVID limbo wasn’t unique to us; it affected thousands of timeshare exits.
In February 2026, the lawyer sent us a 1099 for the cancelled debt. They actually cancelled it in January 2025. Here’s something else you need to know: a timeshare cancellation is a taxable event, so be prepared. I owe thousands in taxes this year because of it. The IRS treats it as income unless you were insolvent at the time. I was not.
Another tactic the timeshares use: they’ll cancel ONE account, but they often have several open. Once the lawyer closes the case out, they can come after you for the rest of them. Someone at Aaronson noticed two account numbers, and I told her about that “right to buy more points” thing, so there is a letter out to Hilton Grand Vacations (they bought Diamond) for ALL account numbers under our names.
Conclusion
We were happy with our September week at Turtle Cay. If nothing had changed hands, we’d probably still be using it today. The problem wasn’t the idea of a fixed week—it was the corporate incentives that came later.
If you find yourself trapped in a system like this, know two things:
1. You’re not stupid.
2. You’re not alone.
There are good attorneys who can get you out, but you need to be aware of the tax consequences and the possibility of multiple accounts hiding under your name. Go in with open eyes. Protect yourself. And don’t let anyone pressure you into believing the problem is you.
What I Wish I Had Known
- Corporate takeovers change everything.
- Points systems are engineered for upgrades, not usability.
- High-pressure sales tactics target your emotions, not your logic.
- Exiting a timeshare is slow, expensive, and taxable.
- You may have more than one account without knowing it.
Note
I don’t believe that any of the individuals I interacted with were evil. Most were doing the job the system expected of them. What I question is how anyone stays in an environment where the goal is to pressure people, often people who clearly cannot afford it, into buying a product anyway. At some point, the system’s incentives overpower basic human empathy. And that’s where everything breaks down.
