Just another perspective... I think
@thomas15 is trying to give you a "most likely for success" suggestion.
But, my own experience is that for 500-800 rounds per month, you can do quite well with a LCT if you have the time (5-6 hours for that amount of reloading including any prep work) and you can reload .40sw for $13-15 per 100 depending on cost of components (after you have acquired your fired brass). I would say you can get a really good start for around $250-300 even including a necessary few items like a vibratory tumbler, calipers, and scale. For pistol reloading... if you get into higher volume-- yes a progressive press would be very nice-- however, I've been very content with loading a number of pistol calibers on my LCT over the years and have turned out quality ammo, consistent in accuracy and reliable in function. (.380acp, 9mm, .45acp, .44magnum, .22TCM) I enjoy the reloading process, and there's always something to tweak (if you are a tinkerer!
). If you are just wanting the ammo, then you can just load away pretty quickly once your loads are developed and your equipment is set up. There's very little adjustment needed-- just double check your produced ammo regularly. A chronograph tells you where you are with velocity but is not necessary for loading good ammo as long as you CAREFULLY FOLLOW YOUR RELOADING DATA IN PUBLISHED MANUALS!
Now, it will take you a while to get your process/procedure sorted out so you can get into a "rhythm" of reloading, but once you get through the learning curve, I bet you will find your rate of production to be acceptable and attainable.
I would love to have a progressive, but it's not necessary for my use, and I have enough time to use a turret press.
The cost would be recovered fairly quickly based on the retail ammo price you quoted.
EDIT: I probably have invested $500+ in my reloading setup, even including multiple die sets. A single caliber can be done for quite a bit less.