Q: How much is this all going to cost. A: Bare minimum $2000.
I think that in the first three or four years after getting my CHL, I might
have spent $2000...and bought and sold about two dozen different handguns in that time. And ended that period with three or four suitable carry pistols.
If you are a smart shopper, and buy used at the right price, especially locally, you will lose essentially nothing in your buying and selling.
You will spend money on ammo and holsters, but even the holsters that do not serve you well may be sold on eBay, with minimal loss.