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Yesterday was the first time in a while that I listened to one of the time share deals in a while. I’ve gotten SPG and Hyatt mailers, and listened to an IHG offer one time. The conversations basically consist of the rep touting all the benefits I will receive before I basically say “thanks, but no” and then do my best to end the conversation and hang up. I had a few minutes to spare after calling in to unfortunately cancel a night booked with me Hilton free night certificate, and decided to let the rep connect me to a “special offer”. I would get 500 Honors points for the trouble.

I knew what I was getting into, and overall, the experience gave me some insight into these “deals.” The rep picked up quickly, much faster than the Hilton Diamond desk (which took 3 minutes) and proceeded to offer me quite the choice.

Las Vegas? Or Orlando?

I literally laughed when she asked which one I’d rather visit. My answer was one word: neither. I’m not a fan of Vegas. And I’m marginally more of a fan of Orlando. This is probably the first travel case where I’m asked to pick the lesser of two evils. Ok, I take that back. Choosing between dealing with United and dealing with Avianca takes that award (SEE: My epic battle with LifeMiles and how I was finally (sort of) victorious).

Rather than ask which one I dislike least, she asked which one I could “see myself in more”. Which meant I had to go with Orlando by default, because, hey, I have kids. Orlando has Disney, and therefore, it is more probable that I will end up in Orlando in the future.

With that settled, she proceeded to give me details of the travel package. The cost was $199 plus tax (about $223 all-in), which would get you three nights at a resort property in Orlando for up to four people. Not a bad deal, even at just face value. She proceeded to tell me all about the activities in the area, even beyond theme parks. The value was pegged at over $900, which seems roughly right for a three night stay. If we had plans to be in Florida at all, I would have seriously considered the offer. The initial offer was for a stay anytime in the next 12 months, no blackout dates (not sure I believe that).

Then there was the one little detail I was waiting for: she told me my wife and I would be “invited” to a two hour presentation where Hilton would showcase …something. She didn’t say the words time share. Can’t remember now what she called them, but that’s what it is.

a man in a grey suit

I’m a very hard sell

Kudos to the rep. She did her best and actually got me thinking about biting on the Hilton package deal that was being offered. But she didn’t know I had no intention of buying. After listening to the details, I simply said, “it sounds nice, but I’m not planning on spending $223 today.” Of course, the pitch didn’t end there.

To sweeten the deal initially, she told me she would extend the offer by an additional six months, giving me a total of 18 months to decide where to stay. It could also be Orlando or Vegas (thanks?). This didn’t make the deal appreciably more tempting. It would give us through next summer, which would be nice. But I’d still be on the hook for $223 now. No thank you.

After I didn’t react to that, she offered a $200 credit for a stay at any Hilton property. I’m not quite buying that this is exactly 100% the case. I’d really like to see the terms. But it would be like getting my $200 back. Now we are at least getting somewhere. But this was still $223 today that I would be spending.

When I declined her generous offer yet again, she then threw in an additional 10,000 Honors points. I told her this was really just another $50, which isn’t all that much. She proceeded to tell me 10,000 points are worth “much more than $50”, which can be true, but only if you know when and where to use them. My base value of $50 does not change, as this is the value you will get across the board 90% of the time.

Then I asked the question: are the $200 certificate and 10,000 points offered up front? I mean, it can’t hurt to ask. My wheels were turning. If I could use the certificate for a work stay, I would effectively be pocketing the points for $23, as I’d get my $200 back. We’d have the option for a 3-night stay down the road, but I could also walk away from the whole time-share deal scot-free if I wanted.

She chuckled. The answer was obviously “no”. Attending that presentation is an absolute must, I see. The conversation ended pretty quickly after that.

Why didn’t I take the offer? First, I’m not sure if we will be at either of those locations and I honestly have little desire to plan a trip to either. Second, it’d need to be both my wife and I, not just a trip with one of the kids where we could head to Vegas for the weekend, so it’d be the whole family. We have yet to travel as a family of five since adopting our three kids over a year ago.

Will I see the offer in the future?

Possibly. Not sure. The rep said the offer would be removed from my account once the points were credited for listening to it. But I highly doubt this is a forever thing, and I honestly wouldn’t be surprised to call into Hilton in the near future and have it offered again. I mean, why stop marketing at someone after the first try, especially if they have shown a little interest?

At the end of the day, I’m not sure 10 full minutes was worth 500 Honors points. But the insight into how they’ll toss more into the package if you play hard to get was honestly worth it. I’ll make sure I do the same next time.

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