I'm pushing 40 and have been shooting recreationally for 15 years, plus another 9 years in the infantry where I shot for a living. I figure I have another 25-30 years of shooting left before the inevitable happens (boredom..lol

).
There are better reasons than savings to get in to reloading, I know... But to be perfectly honest, until my kids leave the home savings will be one of my main reasons to do or (not to do) anything. So like you I'm a big believer in 'buy it once - buy it right'.
The reason why I ask about caliber savings is maybe there's a caliber that I can get into which will help me get past the mental block of spending all that cash...? Savings PLUS accuracy = go. In all likelyhood I will still invest in my own factory, because you guys are all correct - the machine is amortized and brass can be reused 10-50 times (depending on who you talk to); and in the long term you will definitely save cash plus all that extra enjoyment.
Plus where will I get my ammo when the zombie apocalypse happens?.