These threads have come up from time to time over the years and I enjoy reading about the plans others have that are similar to ours.
I couldn't be more pleased to report that there is just one more month to April 4, 2007, when I'll be able to retire. Though I plan to stay until January 6, 2008, when my DW will be able to retire. We work for the same employer.
Wintering at OKW has been our plan since 1995 when we purchased our first master contract. We've purchased several add-ons as well as resales since then bringing us to our current ownership of 1675 points, all at OKW. With these we can stay in a one bedroom villa for 9 weeks, from mid December through mid February. Though our goal is 3000 points which will allow us to stay for the months of November, December, January and February. For this long a stay we'll drive rather than fly and may very well decide to stay a week at HH on the way to WDW then again for another week on the way back home.
We thought our German Shepherd (11 months old, 80 lbs.) would force us to rethink our plans but as it works out our nephew who lives in Orlando, has agreed to take the dog for us while we're at OKW. Very generous of him indeed...just ask my DW.
Looking forward I believe our first extended stay of 4 months will be early November 2010 through late February 2011. The gap between our retirement date and the start of our extended stays is to allow us the time necessary to build our dream house in the lakes region of New Hampshire.
We're both still younger than 50 so we fully expect to be at OKW when whatever happens - happens in 2042.