RE: the age of the OP ...
I started reloading when I was 13 or 14, and I was pretty much self taught as well, my Stepdad did check out what I was doing though... I started with the most basic tool out there, the Lee Loader.. the old hammer the round together one. Graduated to a Lee Challenger press from there. One of my "jobs" during the summers before I was old enough to get a "real job" was to work up handloads for his / our rifles and pistols. I'd work up a load for a particular gun, testing it out back (we lived on 30 acres in the country), and when he got home I'd have a mag full for him to test. I'd show him what I did, what the load was, and he'd go out back and try it out. Granted, I was very meticulous (yeah, a bit nerdy), and was very careful. I see nothing wrong with a teenager learning this skill, sounds like he has supervision. I really did most of the reloading for the household when I was there... I was more careful than my Stepfather was when reloading (he likes to push the envelope a bit further than I do) ... he kept those experimental items separate from the stuff I loaded.
Regarding the original question ... I've got what I consider the ultimate for my needs... well, almost. I quit reloading when I moved out of the house and went to college, but got back into it about 3 months ago... have a shooting buddy that I've known since I was a teenager, and we've been doing bulk ammo buys... and after the last one, I looked at the math and it just didn't add up. Then he pipes up and says he's finally started setting up his Dad's old reloading equipment in the little shed behind his house (his Dad passed away a few years ago)... anyhow, I decided to get onboard (at the age of 32, it's been a while since I pulled a press handle).
I have a progressive setup .. Hornady LnL (Blue is Great... but the Hornady Red is pretty darn good too), scale (beam scale), Hornady / RCBS dies, heavy Craftsman bench with overhead light, digital calipers, Lyman tumbler, a few reloading manuals. I do have one more thing coming to complete the setup, a Lyman case trimmer (for when I get into reloading my .300 Wby). Since I'm mostly reloading pistol, haven't needed the trimmer yet, and all my .30-30 brass is in spec. I can afford whatever I want (not bragging, just don't have a wife or kids to deal with / plan for, and probably won't ever), but I like getting value for my money. The only thing I will probably end up adding is a decent single stage or turret press, probably a Lyman Turret, a Hornady Classic LnL, or an RCBS rockchucker... haven't decided on that yet.
Anyway, to the OP, good to have you here and in the hobby. Always good to have "new blood" in the sport / hobby.