When starting at 375, you won't make it from 308 to 264 in one step. The neck walls are becoming so thick and compressed at that point it's just too much to go 264 from 308. Like I said, 308 to 277 will probably work, 308 to 284 will work for sure. But 308 to 264 is asking for trouble.
You can get 40 thou jumps pretty easy to start, but the more you neck down and the thicker those walls become, the less you are able to jump in one step without getting folds in the neck.
Whatever you do, don't dare use an expander ball when necking down that far. You'll probably be fine with an expander ball from 375 to 338, but after that it can become extremely difficult or even near impossible to remove without damaging the decapping rod or brass.
I was recently necking down Lapua 423 Dakota brass to 300 Norma Magnum. It had been a few years since I necked down that far. I had a brain fart and forgot I left my 30 cal expander ball on the decapping rod when making the final jump to 308. It took a TON of force to get the brass free from the die. If I wouldn't have had the big thick rim inherent to the 416 Rigby parent case, I don't think I would have been able to remove it. Smaller thinner rims would have ripped from the shell holder like they do when a case gets stuck in the die