Personally, I like the dependability that comes with a studded 6.0L. Prior to my HG's and studs, I only ran stock programming.
When should I stud my truck?
That is a question that in reality the owner is the only one who has that answer. A basic tune and exhaust will put around 400HP to the rear wheels, and there are plenty of guys around without studs on that setup. I recommend looking over my Bullet-Proofing thread and come up with a game plan that will work with your build goals and budget. (I wouldn't push performance more than the tune on stock bolts).
Write Up: Bullet-Proofing the 6.0L PSD.
There are a few ways to handle studs
1) A one for one replacement - Only works if you know your heads and gaskets are good, and done at the same time as an oil cooler rebuild and EGR solution.
2) Cab on/off head removal, when the HGs fail - roll of the dice, ideally with a monitor and you not beating on the truck, you should be able to prevent the HG's from letting loose in the first place. However, waiting for the failure could compound the issue by it being at the worst time (like in the middle of a vacation).
3)Cab on/off head removal, before the HGs fail - good particularly because you set the time that the truck goes down, and take the time to ensure the job is done right. (This is my recommendation, and again rebuild/replace your oil cooler and install your EGR solution.)