I'm not the expert on on reloading, but from what I understand:
1) The initial buy-in-- bullet press, tools, gadgets and accoutrments, and such-- is a little steep. You won't start making your money back right away, depending on what you shoot. That is: if you're reloading seriously expensive ammo like .300 WinMag or .450 or some other bog, hot, or exotic rifle or pistol load, your ROI will be better than if you reload something more generic.
2) You have to learn. LIke everything else, you'll fuck up a lot at first.
3) It's a bloody time-consuming pursuit. Even old guys with lots of time whose passion is shooting their own ammo who make relatively small batches of their own ammo will tell you this.
You're best bet might be to start haunting the local gun shows; in my experience, if you go to a show and take the time to comparioson-shop the wares, you will find some sweetheart deals. Lots of good-quality foreign military surplus ammo, for instance (i.e. I bagged 300 rounds of South African military .308 ammo, cherry condition, never opened, for $50). Be sure to wait towards the end of business hours, when the dealers begin marking their stuff down to undersell the competition and increase their total haul for the day.
Some of these shows have guys who sell their own handloads, and will cut you a discount if you give them your own spent brass for a down-payment. But beware: quality will vary. I once bought some 9mm that I took to the range and shot, and that crap smoked up the place like I was firing a fucking musket and did not group well during the short period of time before I stopped because everyone in the couple of lanes to my left and right looked like they wanted to punch me.