For hard to start nuts or ones in a cramped position we use the extra long "rod coupling nuts" and counter bore them for the first couple threads. Many lug nuts are this way where the nut slips onto the stud and can't be cross threaded. Amazon has 10-32 hex coupling nuts and I'd try counter boring with a #7 drill. Be sure to run a 10-32 bolt in and out of the bored nut to make sure there are no burrs. With the nut ready then you CAN'T do anything but start it if you get it over the end of the stud.
