I can tell you what I have used and why my experience has been, not sure if this will help you or not...
Lee brand will save you alot of money. Most of their stuff it high quality. Some of it, not so much.
Press: I have Lee 4 hole turret press with auto-index. I like that I can take the indexer out and go "single stage" style whenever I want. I'm not sure if I like turret or single mode better to be honest. Cons with this press: It spits the spent primers all over the place, makes a big mess. Also you will want a powder checker die, I have the RCBS one:
http://www.midwayusa.com/product/234716/rcbs-powder-checker-die
Best $30 I've spent. Will save you from a double charge or squib. I bought mine after a squib load stuck a bullet in the barrel of a pistol. I also bought a cheap LED light and zip tied it to the frame of the press so I could better see down inside the cases and check them for powder issues.
Scale: I have both digital scale and balance beam old school scale, and use them both. Will use the digital one to save time while adjusting the powder measure, then when I think I have it dialed in, I will confirm the charge with with beam scale, just to be safe. I also like the idea of the beam not needing external power. So I can reload during a power outage if I wanted to, or during the zombie apocalypse LOL. Avoid the Lee beam scale, it is very difficult to read. I have the Redding scale, got it used at a gunshow for $40. I've also used the RCBS scale and it's a good one too. My digital scale is a PACT.
Powder Measure: Again I have both the digital and traditional measures. I find that the digital measure works MUCH better with stick powder than it does with ball or flake. So I use the old school measure with ball and flake and the digital one with stick. My digital measure is the PACT, it works in conjunction with my PACT scale. It's not very quick but it is accurate. My old school measure is a Lee "perfect" powder measure. I have a love-hate relationship with it. It's very accurate and I love the feature that lets you remove the hopper and drain the powder back into the can. On the down side, this thing leaks powder all over the darn place. I'm replacing it with an RCBS measure (I've ordered it already just waiting for it to show up in the mailbox). I decided to go with RCBS because my dad has one that he's been using since before I was born, and it's served him well for many decades, so it must be a quality product. I went with the newer version that has the quick change metering chambers and I'm very eager to try it out.
Tumbler: I have a Hornady tumbler, I think it's called the M2. Been using it for a while and now the bowl is starting to crack. I'm going to try to repair it with epoxy. Aside from the crack this thing has been 100%. I think the crack is my fault, I might have put the lid on too tight, can't blame the tumbler for that.
Dies: Almost all my dies are Lee. They're cheaper than any of other brands out there and as far as I can tell they work just as well, if not better. I like the powder through expander dies. I have an adapter that lets me put my powder measure directly on the die. I have one set of Hornady dies for .280 Remington and I think the quality is actually better on the Lee dies I've got. Also have an RCBS die set for .30 carbine. Everything else I have is Lee.
http://store.gun-guides.com/Perfect-Adapters-_c_12.html
Priming: I've tired several methods of priming and I'm not 100% happy with any of them. If I had to pick one favorite though, it would be the Lee "Auto Prime II" press mounted system. The bad news is that Lee stopped making these a couple years back so if you want one, you have to get it used. I lucked out, found mine used at my LGS for $9.99
Calipers: I have the cheapest non-digital caliper I could find. I think it came from Harbor Freight Tools. It works fine.
Chronograph: You'll want this at some point. Wait until they're on sale. I got a "shooting chrony" on sale for $70 and it works great.
Optional: You might want a hand-held press so you can do some work from the comfort of your recliner. I have a Lee hand press and it's awesome. I made a portable reloading set that all fits inside a .50 caliber ammo can.
http://www.midwayusa.com/product/650614/lee-breech-lock-hand-press-kit?cm_vc=ProductFinding
The "ram prime" that comes with this thing works pretty well too
Hope this helps you out...
Edited to add:
Get several reloading manuals. You can find them used sometimes at bookshops. I like RCBS/Speer and Hornady manuals but I also have Lee and Nosler. It's nice to compare loads between them