Use packing, or moly, grease on any new gasket that you plan on being able to remove multiple times. Ie... Trans gasket, cvt cover gasket, intake gaskets, rubber o rings as long as theyre not Viton, etc. The gasket is not just for resisting rain like some believe, your cover is designed with certain tolerances and should always be put back on. I do not even run a rear pulley cover on majority of my 49cc based scoots, but I do use the gasket so it will be spaced properly. FYI it doesnt have to rain for moisture to get inside there.
Theres a correct way to do things and theres a back woods, hill billy, I guess this will work way. You have the power to chose which way you prefer to care for your investment.