RE: dillon 550?
With a progressive press there's lot going on at once, and at first it may be difficult for a new reloader to keep track of everything and troubleshoot problems when they occur. That being said, I don't think that should scare you away from the 550 press. With the 550, you can run one at a time (like a turrent press) until you become more comfortable with the whole reloading process. In this regard, the 550 is versatile and very forgiving.
The 550 is a great reloading machine that will last for several decades. The one I have is about 20 years old, and it still makes perfect ammo. I use my 550 mainly for pistol ammo, since it's a high volume endeavor. As long as you take the time to learn the machine, I don't see any problem starting your reloading career with a Dillon 550.