OK here's my first swag. At a high level I would recommend a progressive press for any kind of volume reloading. Many folks recommend starting on a single stage press as it is a bit easier to learn on. However, for volume/plinking production you'll eventually wind up with a progressive press anyways. My recommendation would be to learn by inserting a single case and cycling it through all stations, only inserting another case to restart the process once the finished round is ejected into your finished ammo bin. This way you can keep a close eye on all the individual operations as the case is indexed from station to station.
The choice of reloading press will be a big debate with everyone having a different opinion. The Hornady LnL AP is a great starter press. Lee offers a solid option with great value. RCBS also makes good progressive options. And the ultimate in progressive presses is the Dillon. My recommendation would be to buy once, cry once and go with the LnL AP or Dillon. One option would be to lurk for awhile and see if someone offers a used press up for sale. Marcususp frequently sells used presses and he is great to work with.
Please keep in mind each one of these pieces of equipment can support a separate thread in it's own right.
Reloading Manuals (Hornady, Speer, Sierra)
Reloading Bench: A deep topic in it's own right. Mine is bolted to the garage wall studs to minimize bench movement and vibration.
Reloading Press: Good choices for progressive presses are Hornady LnL AP, RCBS, Lee, and Dillon progressives.
Dies: For handgun plan on carbide dies which eliminate the need for case lubing operations. Lee, RCBS, Hornady for good value. Redding also makes great dies as well as Forster.
Powder measure: Largely dictated by your choice of progressive press
Powder Cop/Lockout Die: RCBS and Hornady make good options. I really recommend one of these right off the bat to eliminate dangerous squibs (no or light powder charge) or double powder charge, learn how to adjust the die properly, test it against both conditions, and calibrate/re-check regularly.
Powder scale: You'll need this to spot check and audit the charges thrown by your progressive press powder measure. I can recommend the RCBS Rangemaster for electronic or you can also go mechanical/balance beam if you like (Ohaus makes good mechanical scales).
Primer tray to orient your primers so you can pick them up into the primer tubes (MTM primer turning tray is a good choice)
Primer tubes (Dillon primer tubes are awesome) used to fill up your progressive press priming magazine
Calipers (I prefer mechanical vs electronic, Mitutoyo and Starrett are tops but really expensive, plenty of other options available for good value)
Bullet puller (for the inevitable mistakes
I really like the Hornady Cam-Lock with appropriate collets for the cartridges you're reloading)
This brings us to case tumbling & cleaning. A lot of folks like corncob tumbling media and will have differing opinions. I'm a big fan of stainless steel media. More expensive to tool up initially but your long term costs are cheaper. This can be a huge debate in itself.
Case tumbler (Thumlers tumbler is expensive but great way to go)
Tumbling media (Stainless steel pins)
Case polish (Armour All Ultra Shine Wash & Wax)
Hard water treatment (Lemishine)
Detergent (Partial to Dove detergent)
Media separator (Franklin Armory makes some great options here)