What all is going to be needed to upgrade to a Dillon. Obviously the Press, Only 1 Powder Dispenser and powder die, and a Caliber conversion kit for each caliber.
In addition to the suggestions others have already listed, I would recommend getting a separate tool head and powder die for each cartridge you plan to load. I use the same powder measure for each, but having the dies and adjustments all set up and ready to go sure saves time during changeover.
I also installed one of the UniqueTek micrometers to my large powder bar. It's really handy for dialing in powder charges more quickly, and the fine threads make it much easier to get the powder charge exact.
http://uniquetek.com/product/T1231The Bondus balldriver screwdrivers are the best tools I've found for getting at all of the allen-head cap screws on Dillon presses.
https://www.amazon.com/Bondhus-1063...s&qid=1549816704&s=hi&sr=1-1Other than that, start off slowly. I've let a lot of friends use my Dillon, over the years. They all had previous reloading experience, but they were very careful and deliberate with each action, when they first started using the machine. There's a lot going on with a progressive press, with each pull of the handle, and it can seem a little overwhelming for a new user to try and keep track of it all. My friends quickly got the feel and rhythm of running the 550, and after a few hundred rounds, they wondered how they ever loaded ammo any other way.