You can't go wrong with an RCBS Rockchucker. I see a fair deal on Amazon with free shipping. 1 or 2 month waiting time though. $320.00
Start with your fav pistol caliber because pistol is more forgiving. What is your fav caliber?
Other items you need for semi-auto pistol ammo:
carbide 4-die set (3-dies for revolver)
Analog or digital calipers
primer pocket chamfering tool if using mil brass
small tumbler+media+polish for nice shiny ammo
more loading blocks
reusable ammo boxes are good to have
acetone based carb or brake cleaner (Johnsens non-chlorinated brake cleaner)
Sturdy/heavy table or bench. There are both downward and upward forces
brass-powder-primers-heads obviously
A co-worker or friend that already knows what to do.

When you graduate to rifle loading:
Rifle dies appropriate for your particular rifle
Case trimming tool
neck chamfering tool