With the current low cost of 9x19mm ammo and relatively low cost of 40 S&W ammo, I find it hard to justify reloading for those calibers. During the Great Ammo Famine of 2008-2016 I did reload 9x19mm, but now I just buy it by the case, but I do save my brass for future ammo shortages.
I think you might be able to reload 357 Magnum for quite a bit less than buying factory ammo. I learned reloading with the 357 Magnum. With cast lead bullets, and I would recommend the powder coated variety, you can reload anything from light, target wadcutter loads to mid-range loads and even full power loads. I would stick to 158 grain bullets for full power using cast lead.
As for reloading equipment, this is a big monetary investment. I started with a Lee Challenger kit. I found the O-frame press to be of good quality, but it did not take long to figure out that the dies were not of the highest quality. Lee makes cheap products and cheap they are. Lyman, RCBS, Dillon, Hornady, and Redding are more expensive, but also bring better quality. I think the best value would be RCBS.