The modern drain plugs that are metal with the oring type material in the center really work well, but they are only good for so many times on and off. Back when I was in the repair business I would usually replace them every 3 or 4 oil changes and would never have a problem with a leaking drain plug.
As far as the gaskets go Fel Pro has been a staple for years and they have a top notch product. I have used BEST a few times recently and like the product also. So, horse a piece on the gaskets for me.
Don