I have to agree with Scott on this. The 5.3 is a very capable motor, but if you're looking to stay naturally aspirated and make 400hp at the wheels I would start with a 6.0 or 6.2.
Can your goals be accomplished with a 5.3? Absolutely, but will the power be where you need it in a heavy ass truck. Probably not. What good is 400 hp if it's only available at 7000 rpm? If you're drag racing and have a properly matched combo to that 7000rpm great but I'm assuming this is not going to be a drag only truck and you need some torque to go with it.
6.0/6.2 is the way to go. Better heads and displacement right from the factory. Plus, depending on which one you get you are starting off with close to 400 crank hp.
What are you wanting to do with the truck?
I just want more all around power. More torque at the bottom end to get off the line and more ponies to keep going. I also want more torque to be able to haul trailers that "i cant haul because theyre too heavy" says me dad.
Is your truck still a 4 speed or the 6 speed?
The 5.3 can certainly be made stronger. You would be amazed what can be had just from a custom tune. It will give you more than what many can imagine. I would start there. There is no reason to wait on it until you get other stuff, because just will retune it for free.
That being said. Your 5.3 really is not the limiting factor of you towing more. Gears, suspension, brakes and maybe transmission are more the problem than power. The 5.3 will pull more than the rest of the truck should handle. You may already know this, but I just hate to see people overloading a half ton when I have to be on the road with them.