A rule of thumb with 500 grain 458 Winchester loads. If the powder works well with 50 grain bullets in a .223 Remington, it will work well with 500 grain bullets in the 458 Winchester.
AA 2230 and Ramshot Exterminator (now the same powder) have worked well for me.
H-335 has worked well.
Phil Shoemaker uses IMR 3031. Nuff said.
Woodleigh bullets recommends Hodgdon Benchmark in their reloading manual.
I use a Lee Factory Crimp die to apply a good crimp.
As the 458 Winchester is a short case to begin with, and you need all the neck purchase you can get, only trim 5 thou off the case. 2.495 inches.