JeepJerry,
I'll try to help some. As to the seating die, it is important to adjust the main body down as low as it will go beforeadjusting the stem. I usually put in an empty case, and spin the die body down until it starts to crimp the case (if the die crimps also), or to the point that it starts to remove the bell that I put on it in a previous step. I then adjust the stem for OAL. I use the Lee and CH dies for mine, and have had no issues other than some marks on the seated bullets. Don'y know if this could be part of your problem.
As to the load, I do not have my numbers in front of me, but always start at at least 10% below the published min's. I would say with standard run of the mill calibers, a good book, and eye to pressure signs is usually all that is needed. As the 458 is still a semi-wildcat (or full depending on how define things), a chrony is VERY helpful. Pressure signs for the 458 include extracter and ejecter marks, primer marks and case head expansion. Velocity is very key for me.
As to the number of loads to check, I would say that 10 is high, especially if you see any pressure signs, or velocity is not right. Velocity can be tricky due to barrel variations, but you should be "close" to published. I would say that if you get 3 rounds that are showing some pressure, better check with a chrony before going any further up. If you get clear signs on the first round, I would stop right there. Also, factory loads and a chrony can help you get a feel for whether or not you might have a fast or slow barrel/throat.
There are a lot of variables that are involved in the handloading process. If you are seeing pressure, and your velocity is "low", it could be the brand/type of primer, the seating depth, a fast lot of powder, your steps in sizing, the size of the chamber/throat or a few others. Do not get discouraged if your velocity is way low and you think you are getting excessive pressure. Reloading is a process that can take a fair bit of work, and substuting different components can make a big difference. If you do not have a chrony, perhaps you have a friend with one. I will say this to any new reloader. If you try to get every last bit of velocity from your load, you will probably not have your most accurate load, and you will be on the ragged edge of a minor problem (trashed brass), a big problem (sheared lugs), or a major problem ( a trip to the emergency room). I would heartily encourage you to run your loads through a ballistic program when you get to where you think you want to be. You will find that the extra 50-75 fps means exactly nothing in terms of bullet drop, wind drift and point blank range, in field conditions. No animal or piece of steel can tell the difference.
I am not trying to preach here, but you did mention being new, and I've been there. I have had exactly one blown case in a 460 Rowland in 25 years of handloading a lot of different calibers, and that happened recently. I could have lost a hand. Handloading is not hard, it is just fairly meticulus.
Craig