Reloading has it's benefits and disadvantages. I have been reloading for close to 50 years, and honestly, if I were to start all over I would probably take up knitting.
That said, you need to contemplate a few questions before you truly take the plunge:
First, how many rounds do you anticipate shooting in any given month?
Second, how many different cartridges do you anticipate reloading?
If you plan on shooting under 750 rounds or so a month, spread over a few weeks, or you plan on reloading multiple cartridges, the single stage press would probably be your best choice. However, if you plan to shoot 400 to 500 rounds in any given weekend, a progressive press could be your wisest move, unless you plan on reloading both rifle and pistol cartridges (then get both) .
If you are shooting and reloading just one cartridge family (38/357 or 44 Special/ 44 Magnum) I would give serious consideration to getting a used Dillon Square Deal B in your chosen caliber. When I bought my first SQB, I bought it directly from Dillon for about $198. I have been looking on the popular auction site for a used SDB, and the starting prices have been around $400, with Buy it Now prices going well over a thousand dollars. [My current setup is my original RCBS Reloader Special (rifle cartridges, for priming LPP, and sizing PC bullets) and my Dillon 550B (all pistol cartridges except for 357 Sig).]
Back before prices went out of control, I was able to reload 50 rounds of my cast bullet 38 Special wadcutters for about $0.75, 45 ACP for under a dollar. Now, using current prices and my cast bullets, those same 38 Specials would be closer to $6.00, while the 45s would be about $7.00.
All-in-all, whether you go with a single stage press, turret press, or a progressive press should be influenced by your volume of shooting. Based on my reloading speed, I can resize, prime, charge, then seat the bullets at about 75 rounds per hour. With a progressive, I can usually reload about 200 or more pistol cartridges in an hour.
Note: for when the SHTF, I also have a Lyman 310 tong tool for my revolver cartridges and rifle cartridges.