This is how Ranch Dog got me into reloading several years ago. He just made it too easy. All you need to do is make choices and consider the caliber(s) you will be reloading for.
Courtesy of Ranch Dog:

This page contains ideas to help you get started in reloading ammunition. There are various manuals available that will walk you through the steps or process of reloading but for a quick overview look at Lee Precision’s Reloading Made Easy. The Lee Precision catalog is also a good reference in how the various pieces of equipment are used, so call 262-673-3075 for a catalog or simply click this link to order one from one from the Lee Precision web site. Also, have Hodgdon send you their free reloading manual so that you can start getting an idea on what powders to consider.



The Basics of choosing the equipment



Turret press:

This Press allows all dies to be set up once. You do not have to remove dies for each stage of the operation. The one time setup will eliminates adjustment errors and difference between lots of reloads. Everything remains the same. Additional turret plates can be ordered to mount additional caliber dies on.

Dies:
Lee offers several series of dies. If reloading for levers, autos, or hunting ammo my choice is the Pacesetter series of dies. They full length resize to closer chamber specs than any other dies offered. My experience is that these dies produce extremely accurate ammunition. The set includes a shell holder and reloading data for the specific cartridge. If you are reloading large straight walled cases that use an expanding die (375 Win, 444 Marlin, 45-70), or if the dies are considered Limited Production Dies (32 Win, 35 Rem, 356 Win), the die set does not include the Factory Crimp die. Order it separately.

Case Prep:
The tools will allow you to use a portable electric drill to trim cases, very quick and easy to use with no setup time. The case length gauge is caliber specific and includes a shell holder. These shell holders are numbered the same as press shell holders.

Priming:
The Auto Prime tool uses it own design shell holder but they are numbered the same as press shell holders. If needed for additional caliber.

Powder Handling:
For distributing powder to pistol and rifle, use the Auto-Disk or Pro Auto Disk Powder Measures on the turret press. The Double Disk kit will allow you to charge rifle cases up to 3.43cc (308 Win.). Die sets that do not include a powder through expanding die (straight wall cases), will need to add a Rifle Charging Die. The Swivel Adapter will allow you to change the Powder Measure from one die set to another. The Perfect Powder Measure will be used for load development. The Safety Scale will be used for verifying initial powder charges of the Auto-Disk Powder Measure and Perfect Powder Measure.

So here is what to order:
Turret Press setup
Deluxe Four-Hole Turret Press Kit with Auto-Index, 90928: $79.19
Includes:
Auto-Disk Powder Measure
Safety Powder Scale
Case Cutter and Lock Stud
Chamfer Tool
Primer Pocket Cleaner
Add:
Pacesetter Dies, 90543: $17.99
Factory Crimp Die, 90828: $7.19
Case Length Gauge and Shell Holder, 90150: $2.98
Cutter with Ball Grip, 90275: $2.99
Resizing Lube, 90006... $1.15
Auto Prime, 90230: $8.39
Auto Prime Shell Holder, 90202: $1.79
Double Disk Kit, 90195: $8.99
Swivel Adapter, 90477: $3.59
Rifle Charging Die, 90194: $7.19
Perfect Powder Measure, 90479: $17.99
Modern Reloading, 2nd Edition, 90277... $10.00
MTM Universal Loading Trays, LT-150-43 (2): $6.40
Harbor Freight Digital Calipers: $15.99

Total: $188.65 plus shipping