What's it like driving from Western Europe, say Italy, to Moscow, via parts of former Yugoslavia, Romania, Bulgaria, Poland, Ukraine, etc? What are the border crossings like for an American? Can it even be done next month with the pandemic winding down?
I wouldn't even think of driving to Moscow via Belarus or Ukraine pre / post the pandemic.
I HAVE entered in a non RU vehicle via Latvia ( exiting via Finland ) and my beloved has crossed from Georgia to Russia in a non RU registered Mini van.
As long as you have all proof of your owning the vehicle, your driving license,( get an International Dring Permit ) docs appertaining to the cars VIN, engine capacity, etc., ( you can either buy insurance on crossing the border or source it before you enter RU ) it's not a biggie.
Belarus reiure to you pay a deposit for a tracking devices and you are time limited to cross , may not deviate off the transit route and then you must return the rented tracker and pay for the km used.
So, you would need to take a northern loop via Poland and Lithuania, Latvia or southern .. via Turkey and Georgia ( as the latter crossing in mountainous - forget crossing in winter - unless it is a 4WD fitted with winter tyres)
Winter tyres are a legal requirement from early Nov in most eastern EU nations.
When in Russia, you are unlikely to be stopped by the Police in routine checks