I started reloading in the mid-1970s. The company (Omark) that owned the company my dad worked for also owned Speer, CCI, and RCBS ... so we got our single stage press and dies (plus components) at the employee discount. In the late 1980s I discovered Dillon and bought a SQB, and upgraded to a 550B in the early 1990s. Having shot competitive Service Rifle for over 20 years, and dabbled in IHMSA and NRA 2700s for about 10 years using only handloaded ammunition, I feel that my reloading equipment has more than paid for itself ... so I don't even factor in the cost of my equipment.
In the early 2000s, I started casting my handgun bullets and laid in a generous supply of powder and primers. A fellow Kiwanian ran a junkyard, so I "purchased" a few hundred pounds of wheel weights. At the time I was shooting just 38 Special, 357 Magnum, a (light loaded) 41 Magnum, and 45 ACP. At that time, I could load a box of 38 Special for about $2.60, 357s and 41s for about $3.00, and 45s for about $3.25.
In 2007 I was in an accident that left me disabled, so I didn't shoot/reload/cast for about 7 years. I've been back to reloading since about 2014, and I'm just getting back into casting. All the while I still have a nice supply of 231, 296, BE, Unique, Red Dot, Blue Dot, AA7, Silhouette, RE19 (?), 2520, 4064, and 4895 and a few years worth of primers.
I've set myself up to handle polycoating (under a $60 investment) my bullets since I've gotten into GSSF matches. As such, my handgun ammo (at current prices) will run me about $9-10 a box, still cheaper than current factory ammo, plus the nice factor is, I'm still shooting when others aren't. I'm now able to reload: 38 Special, 357 Magnum, 9mm Luger, 380s, 357 Sig, 40 S&W, 41 Magnum, 44 Special and Magnum plus 45 ACP. Rifle-wise: 223 Rem, 224 Valkyrie, 25-35 Winchester, 270 Winchester, 7 Rem Mag, 308, 30-06, 30 Carbine, 40-65 and 45-70. I can also load my own 12 guage shells. Plus I have the ability to make my own percussion caps as long as I can stockpile roll caps, which seem to have disappeared!
An added benefit of shooting and working GSSF matches is that the Range Officers get to split the brass, since these are lost brass matches!