Im going to be buying a 96-98 1/2ton 2wd shortbed within a few weeks. Not sure on whether Im going to get a regular cab or extended cab yet. Only thing I know for sure is 2wd, shortbed, 5.7L and [lord help me] an automatic. Also either a 5/7 static drop or maybe a tad lower. Either truck equally easy to lower or is one more difficult then the other?

Also, what problem areas should I be looking for? I know the intake gaskets are an issue [have two vortec motors already, both carb'd though] anything else?

The lowering is basically the same. The extended cab may need to have the drivelline support repositioned when you lower the truck. Most reputable manufacturers have already figured that out and it will be covered in your instructions. I would recommend looking at Bell Tech's website and download their instructions, to allow you to read before ordering. I have lowered several trucks and it is easier to do if you lift the bed off of the truck.