I "replaced" a transmission drain plug washer once, because it didn't actually have one.

But otherwise, there is no reason to replace them, I don't see how they can possibly fail. RTV is not needed, it's a compression seal and works very very well.
Just pay attention to where the ring is, like you said it can stick the tranny or the plug and you might not realize it, then it falls off when you're putting it back in. Just get the filter kit and you're good. BTW, the one I bought last time was a cork gasket and it leaked, a neoprene gasket didn't.