Whoa, whoa....peening the pan bolt holes is a good idea but that's not the way to do it.
First inspect the area surrounding each bolt hold. If the circumferences of the holes are bent upward...towards the engine, you need to peen them flat. You need two ball peen hammers. Place the ball in each hole, then tap once or twice on the face of the first hammer with the face of the second.
Fel-Pro now makes a one-piece pan gasket for the Gen 1 SB. It's in their performance gasket line.
As for what to look for that depends on the mileage on the motor. But in general, inspect the bottom of the pan. If you see a lot of small metal fragments, expect trouble and consider an overhaul. If you see a lot of browinsh/black scummy stuff, consider changing your oil more often. If you've got a lot of miles on the engine, pull a rod bearing or two and take a look. If you find a lot of wear or any damage, I'd overhaul the engine. Roll the engine over by hand such that any piston is at TDC and, using a bright flashlight, take a look at the condition of the bores just below the bottom of the piston skirt. If you see a lot of wear or any significant grooves, consider an overhaul.