Your first step is buying the best reference book or what I call Reloading for Dummies or The ABC's of Reloading from Krause Publications.
There are several great reloading manuals of the real kind not the freebee ones! Paperback manuals are good for cross referencing data, at times. For meaty manuals a person can not go wrong with the Lyman48th and Sierra. One must always look at the loads when you compare data. Especially in larger calibers as some data might be using different brass from yours. Case in point Hodgdon used WW brass to work up loads with, whereas Sierra used Fed cases in their 308 Winchester loading information.
Press - Single Stage or Turret presses are the best way to learn before advancing to any kind of progressive press. You will always have need for a single stage press. Redding and RCBS are good sources of all kinds of presses. RCBS Rockchucker Supreme for a single stage and Redding T7 for a turret press are basically the gold standard for press types.
Dies - I like Redding Dies, and I would get the carbide expander ball upgrade for bottle neck rifle cases. Dillon makes carbide rifle sizer dies, but you still need to use case lube and make sure you lube the inside of the case neck, too. I would just stick with regular dies for rifle cartridges. Dillon makes die sets specifically for their press so to speak, meaning that it does not come with a case mouth belling die; Redding makes a set of dies for progressive presses, too. I like Forster competition seaters, and they can be had as an individual item. Dies are pretty much threaded universally, except for Lyman 310 dies, and Dillon dies for the Square Deal N. Accuracy nuts will use hand dies, and they require an arbor press be used.
Shell holders (if the die set doesn't have them like Lee) or the appropriate shell plate for the progressive press. Remember that many shell holders work for more then one cartridge. I would do some home work, especially if you get a Dillon. Some cartridge conversions might only require you to get powder funnel for the new cartridge.
A tumbler will be a good investment, as clean cases will not harm you dies. There are vibratory and rotary tumblers out there. I like corn cob media treated with some Iosso case polish. You can get walnut in bulk at Petco or Pet Smart. Bulk corn cob grit is a great way to reduce the cost of commercially supplied media, because you pay through the nose for the treated media from other vendors.
MTM makes great loading block tray that handles most cartridges.
Case Lube is great for both conventional dies, and to treat your brass used in a progressive press even with carbide dies. That extra lubricity makes the cycling of the press a tad slicker! Dillon spray lube works well for shake and bake application. I like Imperial Die Wax for rifle cartridges when FL sizing.
Case Neck Brush to clean bottleneck rifle cases
Dial Calipers
Case Trimmer (Lee works, but Possum Hollow is better, Wilson makes the best hand powered Lathe trimmer, and Giraud is the best powered Trimmer)
Deburring/Chamfering Tool
Primer Pocket Cleaner and uniformer
Primer Flip Tray is needed for loading pick up tubes for some primer systems like the Dillon.
Priming Tool (I like the RCBS (now even better with universal shell holder, but Sinclair makes the best)
Powder Scale - remember that is always better to have a mechanical scale as a back up to any electronic scale.
Powder Funnel kit with drop tubes especially if you intend to use powders like Varget.
Powder Trickler (used to tweak powder charges )
Powder Measure (nice for faster powder charges it does require a bit of learning curve to get consistent powder charges sort of rhythm thing) standard with progressive presses, but the RCBS Uniflow is nice! Redding makes a better one, and Harrell is the gold standard!
Hammer Type Bullet Puller (for taking down the boo boo's)
Ammo boxes and labels
A notebook for recording your results! Saves covering the same ground twice!
A chronograph is great when working up loads, but is more a luxury in the beginning.
