We're from suburban Milwaukee, too. We own 300 OKW purchased at resale in 1997 and another 100 at BWV. So far, all of our points have been used at
DVC resorts. We've stayed at all of the Florida ones except for BCV.
Back in 96 we started planning a "once-in-a-lifetime" WDW trip. We had one grandaughter at that time, and there was a second on the way. We originally booked a cash 2BR at BWV. When you added up the package, I realized we could be well on our way to 45 years of vacations. And since I take my job as a grandpa seriously, we decided to take the plunge.
We bought our resale sight unseen (we hadn't been to WDW in 15 years, before Epcot was built), but after a lot of internet research. Those were the glory days of resale, let me tell you. Disney wasn't buying things back, so the price was low. And our resale came with free park passes through 1999. It was a no-brainer!
The highlight so far was spending three nights in a beach cottage at VB. But I'm sure there's lots more highlights to come. We're going to HHI for a week in August, and
DCL next year.