Like golf, fishing, and some other hobbies, you can spend all the money you want to and still be one purchase away from success.
Just to see what it was like, I bought a Lee Challenger press. I already had a RCBS Jr press that I bought 45 years ago (used) that is still going strong and a new RCBS. Maybe if I was a lot better shot than what I am, I could tell the difference between the ammo produced by the three presses, but I can't. To that I'll add, I've been reloading for over 45 years and have never felt a need for any sort of turret or automatic press. They may be handy but I'd rather spend the extra money on better scales and dies and stuff that does make a difference. Also, I've reformed quite a bit of brass and never needed one of the "monster" presses that can convert a Miller beer can into a small automobile.
One question I'd like to ask: Do you have any sort of support group? That is to say, friends or such that reload and can mentor you? Someone that will let you use their equipment to get an idea of what you'll really need? Or are you starting out all alone and in the dark? Do you have a place to build a stout bench to work on?? (a Lee loader can be used at the kitchen table)
Steve said K.I.S.S. and I agree however I'd say buy the Lee kit, buy the Lyman #48 reloading book and read the Lee book and the Lyman book cover to cover. THEN buy you a can of powder, 100 primers, 100 bullets and start to reload. Come to us with any problems you encounter. Don 't be shy 'cause I gurarentee that no matter how asinine or stupid a mistake you make, at least one of us has made it before you.
If for some reason that I can't fathom, you decide reloading isn't for you, you've got $100 invested and not the kid's freshman year in college. enjoy.