I load .204Ruger using a Lee Classic turret press and dispense the powder with an RCBS Chargemaster 1500.
I can load a round per minute, easily, once the prep work is done. Trimming is rarely needed. Cleaning takes a matter of 2-3 minutes because all I do is dump the cases in the tumbler, add a little polish and walk away. When it's done, just dump out the media.
I use a Franklin Arsenal case prep machine. Probably spend 1 minute on each case, cleaning the primer pocket, trimming an deburring.
Clean up takes maybe 10 minutes.
I don't know where you get "good" ammo for $23/50. The cheapest of decent ammo is usually about $1/round.
Loading your own will cost about 15-20 cents for the bullet, 3-5 cents for the primer and anywhere from 7-12 cents for the powder, give or take. Properly handled, cases will last AT LEAST 10 shots and can go upwards of 30. Actually, I've not lost a single case to shooting related failure yet, though I'm no high volume shooter and I use Norma cases.
You can certainly be up and loading for ~$500. I have far more than the basic equipment, including a $350 scale and I've not spent over $1,000.