DVCer here (and Annual Pass holder), and first-time Budget-Board posting...
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In short, we seriously budget for our multiple trips per year. Honestly, DVC membership has been in the back of our heads for a really long time, and we adjusted our budgeting to be able to afford it over a number of years.
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Long story...
I have known about DVC since Old Key West opened way back in 1990. I remember looking at the ad in a Reader's Digest and thinking "Ya know, that would be really great to able to do someday". At the time, we were "just married", she had just graduated and I was still a student (with a part-time job) and a few more years until I graduated. We were living in a decent apartment, just starting out - anything more than an occasional $8 pizza or a $12 CD was a big deal for us. No chance of DVC membership happening then, by any stretch of the imagination.
Both of us are professionals, but not of the usual big-money persuasion (my wife is an accountant, I'm an architect - it's not like we're high-powered attorneys or doctors). My wife now has an MBA (she got it in 2005), and I just have a Bachelor's degree. We have been fortunate in our careers, but not overly so. By that I mean neither of us has ever been laid off or fired, promotions have happened, etc. We budget, just like every other family out there. We do live in a traditionally depressed part of the country, so our annual earnings is about 3x the average family earnings for our county. Our house, which we bought in 2000, is almost exactly average for housing costs for our county - so we have a very comfortable mortgage compared to our income. If we were living in a higher-cost part of the country like out west or New England, things would be different for us, I think. We don't buy cars very often or run up high credit card debt (though we do have a bit at times), and neither of us have habits that cost a lot from our disposable income (books are literally our biggest 'vice' dollar-wise, followed by her scrapbooking addiction and my
Lego habit). In other words, we don't blow our cash on booze, cigs, or lottery tix. We eat out maybe 2 or 3 times a week as a family - my wife eats out at lunch most days, while I work through lunch and eat something from here. My parents aren't well-off (in fact they're starting to have problems with transitioning from working-to-retiring financially), hers are respectively a lot more well-off financially (but not 'rich' by any means) - both sets are middle class - no fancy trusts or parental gifts/loans for us.
Over the years since, we had kinda talked about Disney / DVC, usually around the time we would have a windfall of cash come in (like a raise or promotion) but nothing serious ever came of it. Then, our kids started to be of an age where they could really enjoy Disney.
We did our first "modern-era" trip to WDW in Oct. 2001 (our son was 7, our daughter was 2). It was just after 9/11 and we considered postponing it, but we didn't. It was a short trip - 3 or 4 days if I remember, and we stayed at All-Stars Movies. We couldn't see everything we wanted to see that trip, and found ourselves silently planning "the next trip" in our heads. A couple months later, we were remembering the fun trip and she mentioned that she really wanted to go back soon. I did too, and over the course of a few weeks we had a pretty good itinerary planned out for June 2002, planning to stay at POP.
And then she mentioned DVC. We remembered how we had looked into it and half-remembered the 1990 prices to be astronomical (to us back then on a single salary/student working part-time through school). But anyway we seriously looked at it again, contacted a DVC rep, and got some figures for the amount of points we'd been considering. We basically wanted to have the freedom to be able to take 2 weeks' each year (10-12 days) with a few points left over each year. I was still on the fence - the amount of money we were talking about was the equivalent of an inexpensive new car, but we could swing it. She was sold on it right away once we figured out how it wouldn't be such a big stretch for us. I was just concerned that we'd (I'd) eventually get bored of Disney, and then get screwed out of a lot of money if we tried to sell out years down the road (timeshares as a general rule-of-thumb are usually not great investments). The alternate destinations offerings - not sure what they're called in DVC-Speak - helped me out (basically, DVC has agreements with resorts and hotels around the world that you can use DVC points there), just in case I'll turn into a no-Disney geezer in my old age.
So for our June 2002 trip we thought we'd spring for a Wilderness Lodge stay at a bit longer duration - I think we stayed 5 days. I had just started a new job the month before with a good salary improvement over my previous job. Wilderness Lodge approaches DVC quality for size of studio, so that I could get a good idea of what it'd be like before I ponied up the dough. Also, we walked around the Villas at Wilderness Lodge and talked to CMs, swam in the VWL pool (I prefer quieter pools over the mega-ginormous pools most of the time). I was fine with the idea of DVC after that trip.
Now, how to actually make it happen?
Well, we have a general rule that every other year (or so), one of us has the option of a new car, finances allowing, and we each take turns in that arrangement. Now, remember that neither of us are "Loaded-with-every-option-BMW" type of people, so these really are basic cars. We can 'afford' more, but that's really not what we want to do / or how we want to live. Since 2003 was my wife's year to trade up for a new car - she chose to postpone it a year so that we could do DVC. And that's basically how we did it. We bought points in Beach Club Villas in March 2003. Our choices at the time were a few of the very last units at VWL, BCV, and BWV - Beach Club was my preference since it's so close to Epcot World Showcase (my favorite park), and we much preferred Beach Club over Boardwalk. We do have a DVC financial plan, which will be paid off in the next couple of years.
In 2004 I co-founded an architectural firm with one other partner (he's the majority partner, I'm a junior partner). We have had an additional majority partner join the firm since, and we also have started a development company to build houses - the plan for that company is to eventually branch out into commercial development. Since they're both start-up companies, most of each partner's spare income is invested back into the companies, and the vast majority of my own current debt is tied to loans that each partner has personally guaranteed as part of our businesses. But that will change for the better, with time. I also consider that to be a big portion of my kids' education funding, and our retirement potential (but I'm one of those people who like what they do and will work until I'm 80 if my health allows it).
Also in 2004, we realized we had taken many, many WDW trips in the past 3 years, with many more planned in the immediate future. And so we started looking into getting Annual Passes. We figured that we'd break-even at 6 or 7 days in park each year vs. Park Hoppers. Plus, both APs and DVC allows major discounts at in-park restaurants, shops, and Downtown Disney.
Earlier this year, we were able to buy a small add-on point package for Animal Kingdom Villas to our DVC. My wife has been doing a couple of part-time jobs on the side, and her earnings from those (along with me postponing my 2005 car trade-up for a couple of years to be able to start our company in 2004) allowed us to be able to do that. The AKV add-on package was bought and paid-for, no long-term financing required.
So now, instead of budgeting for 2 or 3 smaller separate WDW trips, we budget for the monthly DVC payments, the DVC annual dues (comes in January), and AP renewal (comes in September). At first it was a big pain when we were making the budget transitions, but now it's smooth. If we think we'll have a year or two when we'll be unable to make enough WDW trips to make it worth our APs, we just won't renew them. Also, DVC has proven to be one of the very few timeshare packages to actually increase in value over time, which is a pleasant feeling. Disney does put a lot of resources into DVC, but it has proven to be worth it to them, otherwise I don't see why they would have continued it for almost 20 years. It's continuing to grow and gets better each year, in my opinion.
The last time I ran the numbers (in late August 2007), it costs us (a family of 4) just under $200 per day to do Disney. That assumes we spend 12 days at WDW each year - if it's only 10 days, it's slightly higher (about $205 per day). It includes the cost of DVC financing (pro-rated/amortized over 30+ years, which is the length of our DVC contracts (30-year for BCV, 40-year for AKV) and the estimated annual dues, travel costs,
DDP, AP renewal, and our usual spending money. I finally got "my" next car in August 2007, a 2007 Dodge Grand Caravan, and luckily we were able to swing it so that I was able to retain my previous car (a 2001 Pontiac Trans Am). Honestly, the Grand Caravan will be mostly used for very occasional local mule-work, and our WDW trips, to the tune of about 8-9K miles per year. It really does sit in the driveway 6 days out of the week, usually. Our daily driver is a 2004 Subaru Legacy wagon, and we carpool almost everyday since her office and mine are within 4 blocks of each other. Since the new van is used basically as our primary WDW transportation - I also ran our vacation numbers with its costs included (yeah, I'm a numbers geek). With it included (pro-rated payments and cost-of-ownership stuff like insurance costs and assumed wear-&-tear), along with trip gas purchases, it knocks our WDW vacation per-day costs to about $250 for 12 days at WDW each year ($265 per-day for 10 days per year). As we get older (meaning more solo "adults-only" trips in smaller suites than we do now), and the DVC contract is paid for, that will be much less per day for us each passing year (which I assume also will be offset by higher & higher annual maintenance fees as the buildings get older). An honest, non-Disney vacation costs assessment would probably be around $150-$200 per day for us, by the way.
This last year, we were very fortunate to swing four separate trips. We did an Adults-Only trip in March for 7 days with DVCer friends (stayed at OKW in separate suites, and our friends are husband & wife, no kids), an entire-family trip in June for 3 days at WDW (stayed off-site in separate suites) / 5 days (in separate suites) at DVC's Vero Beach with same DVCer friends, a 5 day solo family trip in August (stayed at OKW again), and a 7 day extended family trip in October (w/ my in-laws & one of my son's friends tagged along in a 2-bedroom suite).
So we were in WDW an awesome 22 days in 2007, and it would be 27 days if you count our Vero Beach stay (which I would). Since we had so many extra people along for a bunch of those days, and we also shared points with our DVC friends for the two trips we took (we borrowed some points from them for our co-March trip, and they borrowed a few points from us for our co-June trip), it would hurt my head too much to figure out those costs. My W.A.G. (Wild A$$ Guess) for per-day costs would be somewhere around $150 per-day for our 2007 trips, though - maybe a bit lower, maybe a bit higher.
Hope that helps put some light on multiple-trips-per-year-people, as an example of our experience.