Reflection - It was over 25 Years Ago

Today, sitting in a very nice two-bedroom Timeshare in Gatlinburg, TN - Thinking back — it was about 25 years ago.

Donna and I were engaged. Living together with Keara. Starting life. Starting bills. Starting responsibilities.

We did one of those “3 Nights for Only $49” deals in the Berkshires of Massachusetts. It was a nice mountain resort. We had a good time. Yes, we attended the sales pitch.

And I got sucked into the vortex.

I purchased a deeded timeshare.

Let me say this clearly:

Tip #1: Never purchase a deeded timeshare.

You want a trust.
You want a points-based system.
You never want part ownership in a single property.

After we got home, the buyer’s remorse hit hard.

I was already in debt. I couldn’t afford more debt.

Which I had just signed up for.

I couldn’t sleep. I remember lying awake thinking, I just made one of the worst financial decisions of my life.

There is usually a clause in these contracts — often 3 to 5 days — where you can rescind and cancel.

Tip #2: Make sure that clause exists before you sign anything.

I made the call.
I cancelled the contract.
And I felt immediate relief.

This had to have been in the late 1990s.

Since then, we’ve done a handful of other “3 Nights for $49” stays. We listened. We smiled. We said no. We left.

We never purchased again — because we couldn’t afford it.

Tip #3: If you can’t pay for it, you most likely can’t afford it.

Remember, the company — and the commission-based salespeople — make money not only on the sale, but on the loan you just signed. At that moment, do you really understand your total cost of ownership and what you’re getting in return?

Most likely not.

Thankfully, we didn’t purchase anything else from one of those high-pressure stays… until January 2025 at the Hollywood Beach Tower in Hollywood, Florida.

And this time it was different:

- It was not a deeded property.
- There was a clear exit clause.
- We could afford it — cash.
- We earned airline miles.
- We knew exactly what we were paying: $1,900.
- We were retired and had flexibility in our travel dates (off-season travel saves you tons of points/money - you cost per stay goes way down.

- We knew we would get at least one week in Maui — which, to us, made it worth it.

And here’s a small spoiler alert:

We got more than the Hawaii Trip! That's what this series of post are about.Read more