Bent Water is a long drive to schools or shopping, and there are ongoing fees that will eat your saving up. Very nice if you want to pay for the amenities and drive a long way to everything.
Katy is becoming much more densely populated, and the number of apartments has skyrocketed. New apartments today typically means declining public schools tomorrow. I already dislike going into Katy Mills Mall because of the demographic changes and the subsequent change in the store mix that resulted - we just go in and out of Bass Pro without bothering with the rest of it anymore.
I don't like The Woodlands as much as everybody else apparently does. You don't get a lot of house for your money compared to other suburbs, and most homes are on small lots (that's how they can have large common green spaces and keep the lot yield up). Most of the public schools have good stats but the high schools are very large and very competitive, which forces kids to specialize too early. You aren't going to TWHS and get to try out a wide range of sports and extracurricular activities to discover where your interests lie. You have to show up already targeting a narrow range of activities so you can focus your energy enough to compete with the large number of other kids doing the same thing.
We have been looking in SW Montgomery County, around the High Meadow area as well. Be aware that there are lots of starter homes in generic subdivisions being built out that way, which will change the area from semi-rural to suburban. Eventually more apartments will follow, changing the nice suburb to a crappy suburb. That's just the life cycle of Houston suburban development. Also, the public schools serving High Meadow are atrocious. That's about as far out as we can go and still be within a bearable drive of the kids current private school, and we figure the area will stay nice until the kids are off to college.