For me, the Hilton Grand Vacation Club timeshare numbers didn't end up working

A pal of mine emailed me a few days ago asking:

Do you have a hilton grand vacations hgvc timeshare? Which resort do you usually go to? Are you happy with it?

We went back and forth in email, including me explaining some of the math behind time shares and why they're such a bad idea for most people (myself included, in hindsight) and so I thought I'd publish the back and forth here, add some additional comments, and invite you readers to add your own two cents and your experiences with timeshares, whether you jumped or not.

Ready? Here we go...

I responded: We paid $110,000 for a double-timeshare share at the fanciest new King's Land location in the Waikaloa Beach area (Kona Coast) of the Big Island of Hawaii. When Linda and I separated, however, and we took a two-location, shared kids, trip to Hawaii for a few weeks, she booked through Hilton Grand Vacations and I just went to the vacation rentals by owner (VRBO) Web site and booked a nicer place with far, far less hassle.

The theory of timeshares is good, but my experience is that the reality is that it's so complicated to figure out their point system and when you can / can't get what you want, when you want, that I strongly suggest you put the money into a CD and use sites like vrbo.com to book your trips instead.

For example, check out this page to see how many rentals there are on just the Waikoloa coast area on the west side of the Big Island of Hawaii.

My friend, rather surprised to get this information from me (I think he expected it was a better deal), responded:

Thanks for the straight scoop, that's very sobering. You were one of the few people I know who had bought a timeshare and I thought you were still high on it.

We would only buy one on the used market but I think we're leaning away even from that. The annual fees scare me and it seems like they can increase them at will. I like the idea of renting other people's timeshares -- there is a huge market for that and lots of bargains.
Also, VRBO looks great.

My response:

Yeah, ultimately it's about complexity. I really like being able to just go where I want, when I want, and timeshares only work if you actually use them annually for at least 20 years, then the math starts to work in your favor.

I mean, our Hawaiian timeshare was about $110k plus I think $2k/annual fee and a $180 booking fee per trip. My VRBO condo was about $1300/week (maybe?) for a two bedroom. We planned on using it 2-3 weeks/year, so that's $2,600-$3,900 flat fee versus $110,000. How many years do you have to actually go on vacation before the numbers balance out?

To be fair, I will say that the rooms and the facilities are gorgeous. Here's a typical King's Land room:

Nice, eh? But if we would have gone for two weeks every year for a decade then run out of steam and stop using it, that room would cost me about ($110,000/10)/2 per week, or an impressive $5,500/week. At that rate I want a butler, cook and driver thrown in, and probably a private jet to get me to Hawaii in the first place.

The worst thing is that of course that's not the full math because there's at least a $2200 annual fee and that $180/trip booking fee too, so let's say $6,000 per week, paid in advance.

Now there are definitely people who groove on timeshares, but I expect that they have less expensive options, and indeed, I should point out that the King's Land Hilton Grand Vacation Club resort is one of the most expensive ones in the entire chain, and that if were were willing to stay in the older HGVC resorts in Waikoloa Beach, we'd have had enough points for a month/year there. So that's $2,500/week across a decade, but again, the math doesn't quite work out that nicely and there's no mention of the fact that nailing down what we wanted, when we wanted it, was a pain in the booty.

Nonetheless, my kids are very flexible when it comes to vacations, so if I go back to the VRBO site and look for two or three bedroom condos available for a week, it's about five minutes to find a three-bedroom + loft condo in a great location about a half-mile from the King's Land Resort, priced at $199/night (or $1,393/week):

[see more info] [makes me want to book and go out there for a few weeks, actually!]

In a nutshell, timeshares seem to be a relatively obsolete concept to me with the rise of Internet-based vacation rental sites like VRBO.com. If you have the ability to dig around, why go through the hassle and tie up your cash in advance?