For starters, get a books titled "The ABCs of Reloading". It is straightforward and thorough, but none of that "long haired" language that makes for a hard read. I've loaned my copies to several who expressed interest in reloading.

If you can, find a mentor; someone mature enough to provide safe and patient instruction.

Some places, like Sportsmans Warehouse or Gander Mountain stores, will host basic reloading classes. It makes it pretty handy as they usually demonstrate equipment you can buy right there in the store.

Start with a basic O press. Get a good set of carbide dies for the 40 S&W and some full length dies for the 308.

Unless you shoot thousands of rounds a year, the economics of reloading aren't terribly compelling. For me, reloading was a natural progression of learning ballistics. I wanted to learn more control over the variables, and reloading affords me the opportunity to maximize the optimization. Once I started shooting competition, reloading allowed me to tune my rounds to the guns I use, and still saved me a few bucks.

It also made the transition to muzzleloading fairly straightforward.