Personally, I prefer the ones that have community pools, which eliminates a lot of the ones off of Bryan/Yale/Eastwood/Southwood. Racquetclub is a little older and feels a bit more run down, IMO.
If you have younger kids that are elementary school aged or younger, I would choose Park Place/Park Paseo (the same HOA, just depends which side of Yale you're on) over Woodside. You'll feel a little more connected to the school. The pool at Park Place always has kids playing in the summer but the Woodside pool is often empty. You're also closer to the school (Santiago Hills). Woodside has two models that are bigger than the biggest one in Park Place, so that is something to consider. Park Place also has no models with a three car garage; Woodside has a few. However, most homes in Woodside with a 3-car have no driveway.
Bottom line for me: I live in Woodside because I like the floorplan of my house more than I do any of the Park Place homes. But, I constantly wish I lived in Park Place to be closer to the school, closer to my kids' friends, and to have the nicer HOA (better pool, clubhouse, etc).
If you like gated communities (I don't), look at Windstream and Canyon Creek. I think the CC homes are a little nicer, but with a new development coming just on the other side, there will be a few years of construction dust and noise.
Overall, I'm glad I chose an older neighborhood over a new one. We don't have quite as much sense of community as you get in a place like Woodbury, but we have bigger yards and, in many cases, bigger secondary bedrooms and no mello roos.
