Janice---you mentioned that you wanted to stick to the trails. In my limited experience in the Winds (just two trips that each incorporated some easy off-trail travel), the line is often blurry between "off-trail" vs. "on-trail" segments. Some of the "trails" become difficult to follow and I would recommend treating it as if it were off-trail in terms of navigation (bring a map and compass, get a GPS app on your phone, play around on Google Earth beforehand, read trip reports for the area, etc). Many of the on-trail routes also have poor signage, streams to cross with no bridge, etc. On the flip side, some of the supposedly "off-trail" routes have nice use trails that aren't too hard to follow. The only time I ever took a wrong turn in the Winds was when I was on-trail, but ended up following a side trail for a ways before I realized that I was heading the wrong direction and into the wrong basin---if I wasn't paying attention to map/compass, who knows how long I would have gone the wrong way. My point is, I would prepare mentally for off-trail (unless you stick to only the very most popular trails like the trail to Island Lake or the trail to the Cirque from Big Sandy, but I would highly recommend NOT sticking to those trails!), even if your route is completely on-trail. But I would also recommend trying out an off-trail route! Nancy Pallister's book provides detailed info (including maps, description of difficulty levels, etc.) for a number of partially-off-trail routes, and this book plus the Winds has really made me fall in love with venturing off-trail. Some of the off-trail routes there are not hard to navigate and are not overly difficult or dangerous as long as you allocate more time per mile hiked.
As far as where to go---on my first trip there I did a loop that included Titcomb basin (which was the must-see for me), and it was not my favorite part of the trip. I'm not sure if it was even in my top 3 for that trip. On my 2nd trip I did a loop that included the Cirque of Towers (which was a must-see for me), and I don't even know if that was in my top 5 of places on that trip. So I agree with those that recommend visiting some of the less-traveled areas. It's all spectacular up there once you get a handful of miles from those trailheads.