So, if I am buying 9mm at $10/box and .45 at $15/box, it will take quite some time to get my ROI on my reloading equipment back unless I am missing something.
Granted, 9mm isn't the greatest example of the potential cost savings, but you got to understand you can't compare the example of what Leo CHOOSES to load to the ammo you get for $10.00 a box. I don't know Leo, but I'd be willing to bet his loads are of much higher quality than the valued priced $10.00 stuff... Note the example you cited was using jacketed bullets rather than plated or cast and Leo is an experienced reloader that is loading for his specific weapon/needs...
The beauty of reloading is you choose what components you want to load, thus having huge control of the cost.
Decide exactly what you want to load and compare accordingly... If you are only looking to load target ammo, then figure by pricing cast or plated bullets and comparing this to your basic target ammo. If you are looking to load your own SD ammo, then you'll more than likely want to figure in the price of a quality, jacketed bullet and comparing this to the premium line of SD ammo. In both cases, there will be a savings but more importantly, you will be producing much better quality ammo.
In over 25 years of reloading, I have never really put too much effort into breaking it down to how much each round costs me to load... Saying that though, savings is a huge factor to me. I'd say cast and plated are probably 90% of what I shoot, but I look at it from a little different angle than simply cost per round... I rather view it as just how much I can get for, lets say, $100, 500, or 1000... Simply spend an hour online and take an arbitrary $ amount... Shop around for both loaded ammunition and components for the dollar amount you choose... Compare what you get for that amount. That's what, IMO, along with better quality ammo, makes loading your own a no brainer...