Headed to Siberia/Mongolia/stans in 2020 I will only be taking one riding jacket, pants and boots. One pair of offbike footware, most likely something minimal and light, I'm thinking a pair of Sanuks big enough I can wear socks, typically I wear Sanuks barefoot. People will talk to you all days long about to pack and what not to pack but the only way to know for sure is to learn what works for you. Either way from your description you are considering waaay too much gear, if you really want that much crap pack your car.