Re: How to get started reloading..
+1 on doing some reading first. When I started reloading I did a lot of forum searches here and at accurate reloading. There is a ton of info and pretty honest product reviews - you can generally tell who has an agenda . . .
What you get is going to depend on what type of reloading you are going to be doing:
If high precision rifle reloads are your goal, a single stage press of any brand should do you fine. I would recommend spending on your dies - I've had awesome luck (consistency, concentricity, quality) with Redding Match dies.
If you reload in quantity, are looking to save $, and think big O is going to tax the snot out of factory ammo (sounds like you do, and I aint arguing) I would strongly recommend a progressive press. I personally have a hornady LNL AP, and it has been reliable and problem free. I do not have the casefeeder or bulletfeeder and it is fast enough for my needs. I have also heard great things about Dillon progressives, but have never used one.
Whichever way you go, invest in a way to measure consistently - go/no go gauges for pistol (I like Wilson) and a headspace gauge for rifle (I have the Hornady set and it lets me compare against fired loads, which has worked for me). Measure the crap out of everything and load safe!!