So, Hawk, here's what I'm seeing:
3 annual trips x 14 nights each, including weekends
Family of 5, sometimes 6 traveling
Need a 2BR DVC or need 1 room at POR, sometimes 2 rooms
Like the large rooms, food courts, many pools
Rent a car, using the bus for MK
Eat off-property, use PAPs for passes
Paying 130/room/night max, usually
May visit WDW less often in a decade or so
May consider offsite vacations
You're planning one trip in February - what time of year for the other two? Are they usually during the same calendar weeks each year???
Here's what it would "cost" you with DVC - with some assumptions for the above statements.
263 points per February week at OKW (lowest points req'd, Dream season)
x 2 weeks per stay (actually may use 3 times this, for 3 annual trips)
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526 points per 2-week trip per year
x $89 resale purchase price per point
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~$46,814 plus closing costs (you'd have to buy more, contracts are not readily available for this exact number of points)
This would buy you 2 weeks in a 2BR at OKW in Dream season.
526 pts. x $4 maint fees =
~$2100 per year in maint fees for 263 pts, worth a 2-week stay in a 2BR.
$130/nt POR x 14 nights =
$1820 for a 2-week stay in a POR hotel room - and no upfront costs. Double this for trips when you actually need 2 rooms.
It is clearly cheaper to keep getting the AP rate rooms, considering that they've been available for a very long time now and you may only be needing them for another decade -AND- they require NO investment upfront. Granted, there's a BIG difference in the quality and space between a single moderate hotel room and a 2BR suite/condo. However, there is a price to pay for this upgrade when staying onsite in a Disney property. Whether it's worthwhile to you or not - depends on YOU.
Alternatively, you could be paying less (sometimes MUCH less) than $1400 for those 2 weeks in a 2BR timeshare condo rental offsite - regardless of whether you bring the oldest with you or not. You could also be paying
more for a deluxe hotel room onsite or a cash rental of a 2BR onsite.
For OUR family (also 5 people), we found that we loved the space, comfort, convenience of a kitchen, 2 bedrooms and 2 full bathrooms with teenagers. A hotel room is not good for our family during vacations longer than a couple of days. But DVC was too pricy for us. I think DVC is not always the best for families of 5 people.
Like, you, we are fine with driving our car and eating at offsite restaurants (many good ones nearby).

So we are very happy in our offsite timeshare resorts. For some people, onsite is "da bomb" and offsite simply would not make them happy. There was a recent thread on the Orlando Hotels forum, asking why people did NOT buy DVC - many prefer the feel of a hotel room and want daily housekeeping included with the room. To each their own. You'll have to choose what matters most for your family and the price you're willing to pay for it. HTH!
