Check out the Dillon 550B,
http://www.dillonprecision.com/#/Dillon_Reloading_Machines-8-1.html . It's just about the gold standard for pistols and rifles.
I've gone back and forth about this for years, but the $$ doesnt add up for me. The white box from walmart is the same price as the supplies to reload my .40. 9mm from Walmart is even cheaper.
If you want to make custom loads reloading is a requirement. For plinking a common caliber it's too much work and walmart ammo is so cheap. Dont forget; supplies are more expense now too.