Personally I'm a fan of RCBS products and I've been using their single stage press for years. I'm currently using my single stage press to reload 4 pistol and 5 rifle calibers, including 308 WIN. Using a single stage press gives you a "quality over quantity" approach since you're doing each stage of reloading one at a time. I'm not a high volume reloader anyways. With that said, here's what I recommend:
RCBS Kit with just about everything you need to get started for $280:
http://www.midwayusa.com/product/937...tage-press-kit
RCBS Powder Stand for $18.50:
http://www.midwayusa.com/product/125...-measure-stand
If you spend an additional $2.00+ on RCBS gear, you'll be qualified for a $75 rebate:
http://media.midwayusa.com/cms/rebat...n1_dec31_c.pdf
Now you just need to get a trimmer, tumbler, calipers, and what ever set of dies/shellholder you want. Having more than one reloading manual is good to cross reference data. If you decide to want those previously mentioned items made by RCBS, wait until January to purchase them because the rebate should reset for the new year.
Then you'll want to start looking at brass, powder, bullets, and primers. Hopefully you've been saving your once fired 308 brass. Will you be reloading your 308 WIN for a semi-auto or bolt action?