Im the original owner on a 2008 ext cab LTZ 1500. Currently it has 187k miles on it, and (knock on wood) doesn't drip a drop of any fluids and runs just as good as the day I bought it. I've driven it on several long road trips with three adults, it would of been nice to have a crew cab - but the ext cab did work just fine - plus it was nice to have the bigger bed space. I could definitly see how a crew cab would be best in a family/baby situation. I will probably look at that next.
Truck still has the original ball joints and I have (again knock on wood) never done any major repairs to it. I am very meticulous on replacing all fluids on schedule (diff, trans, engine, etc) and it has treated me well. As mentioned earlier in this thread, the paint does seem very "thin" on these trucks and does chip/scratch easily. I have actually had the truck repainted twice - the first time was because it was "sandblasted" in a windstorm and all the paint chipped off and the second time was when a lady backed into the back end of the bed. Now the paint seems to hold up better - as its on so thick
. I head that all newer verticals have issues with paint because they are a different chemical makeup for EPA friendliness and everyone is trying to make them lighter for MPG's.
I would not buy a pre 2014 Silverado at this point, with the new body style I think you will notice a bigger drop in value as they become less desirable. I would save up for a 2014+.
Another consideration is the new Chevy Colorado/Canyons. The new GMC's look awesome, a crew cab could fit all your people and pull a ski trailer easily. Plus it will get much better MPG's then any full size - also I think the price will be under 30k for a fully loaded truck. I also heard that they are planning on a duramax version which would be sweet!
http://www.autoblog.com/2014/07/29/gm-thinks-colorado-canyon-lure-cuv-buyers/