I've leased 2 Winstars over the past 4 1/2 years. Once you get over the fact that you're driving a minivan rather than a convertible, there's a lot to enjoy. The Winstar is a big, safe, comfortable mini-van that may frustrate you in other ways.
POSITIVES:
1. Ranked as the #1 in terms of safety, according to the National Highway Safety web site. Honda's minvan is trying to challenge this but my reading from the published reports tells me that the Winstar is still out front.
2. Comfort. A soft, easy ride, considering that you are in a minivan.
3. The extras: We bought an LX which came with leather tilt seats, decent stereo. Plenty of cup holders.
4. Great storage. Fill it up. It's hard to do but the roof rack will hold even more. Nice hooks and latches all over.
NEGATIVES:
1. Quality: Things that break and get fixed break again and again. For example the traction control system has been repaired at least twice. Luckily it was under warranty otherwise it would have cost $1,000. On the other hand there's a lot built into the vehicles that we've never had trouble with (but I am not about to "jinx" ourselves by listing them!)
2. Service: Adequate but not what you expect when you pay $25,000+ for a car.
3. Big and bulky. If you're a first time driver BEWARE: don't run into beams and posts in parking garages. It happens a lot because the vehicle is bigger than it seems. Once you get used to it it's not too bad.
4. Expensive: not only to buy but to maintain. I purchased the extended warranty because I learned from owning my first Winstar that it would pay for itself. It did. See below.
5. Tires: The Winstar needs to be redesigned so that you don't go through tires every 20,000 miles. This has occurred on several occasions with both vehicles that we've leased even with relatively frequent rotation and balancing of the tires.
OVERALL: If you want a minivan and safety is your top concern, I'd strongly consider a Winstar. When our lease expires next year we'll look at the new Winstars but may go with the Honda Odyssey, depending on the newest safety reports and availability.