You'll need to do an honest assessment of your needs and abilities and try to match the equipment to fit that.

1. The volume of ammo you want.
2. The time available to load.
3. Your own mechanical aptitude.

I started with a single stage and shortly regretted it and upgraded to a progressive. Why?

Do you expect to reload a lot of ammo? 200 rounds a month is one thing. 200 rounds a week is another. Depending on how much time you have available. At the time I started I had a job that required overtime, two small children, a house......

I don't do well with simple repetitive tasks. Sitting there batch processing on a single stage actually bores me to death. For me, it's actually less safe than a progressive. When I get bored my mind has a hard time focusing on the task at hand.

I am however fascinated by more complex machinery and enjoy using it and watching it work. Which is probably why I spent my entire working life with equipment far more complicated that any reloading press. It's easier for me to pay attention on a progressive. But that's me.

If you are not mechanically inclined start with the single stage.

But don't get too hung up on single-stage vs progressive. Everybody I know with a progressive also has a single stage. Sometimes it's just easier to use the single stage for a small quantity of test loads than to convert the progressive. So it's your call. The single stage is less expensive and if the hobby doesn't stick you won't have as much at risk. Just be aware that if it does stick you'll probably want a progressive if you're primarily a handgun shooter. We tend to go through a lot of ammo.