If you treat a cast iron skillet gently, you should never have to reseason it. When it is new, coat it inside and out with a thin coat of oil, put it UPSIDE down in the oven with aluminum foil to catch the drippings and bake at 350 for at least 2 hours.
If you have a pan that is rusty or the seasoning is messed up, clean it thoroughly and reseason. I have used steel wool with a handful of sand as an abrasive for a really bad looking pan, but if you have a sandblaster go for it. Others use lye or oven cleaner spray (never done it myself). Get the grunge and rust off of it and then reseason it.
Rules for cast iron care:
Never use soap - use hot water and a scrub pad. Or for dried on crud, a handful of salt and scrub like mad. (It really works)
Never put food into it until it is oiled and is hot.
Never soak in water for prolonged periods of time.
Always clean up right after you use it.
Never put it away wet.
Don't cook strongly acidic foods like tomato sauce in it.
If you follow those rules, you can pass your pan down to your great grand kids and it'll be as good as ever.