Most people loading for semi-auto pistols tend to go through a lot of ammo. These people would be better served with either a Lee Classic Turret press or one of the progressive presses.
Progressive presses are more complicated and you do have more things to watch. This can be difficult for a person just starting out loading. The Dillon 550b press has manual indexing and in my opinion is easier to learn to operate of all the progressive presses. Dillon will send you replacement parts if they are ever needed at no additional cost. You do pay for this when you buy the press. If you are going to be loading a lot of ammo for many years to come I suggest getting a Dillon press. There are plenty of people who started loading on a progressive press and are still using them today. You also will spend a lot of money on components to load a lot of pistol ammo each month. It is just one more thing to think about.
For someone with plenty of time and only needing to load a box or two of ammo per week, there are plenty of good single stage presses available. A long time ago I loaded a couple of boxes of .38 Special a week on a Rock Chucker press. It made great ammo and served my needs at that time. For precision rifle ammo, I think you can't do better than a good single stage press.
Many people start out with one press and are happy with it. Some will find as they use their press for a while they want other features or more speed and add another press. It is not a one size fits all hobby.
If you are only shooting a box of shotgun shells a month you probably will find just buying factory ammo the best option. When I was shooting skeet a fair amount back in the day, I used a MEC 600 Jr. It allowed me to produce the amount of ammo I needed and was easy to use. It wasn't nearly as fast as a progressive press but I didn't really need one either.
Now I only load pistol ammo. I have a couple of Dillon presses. One is for everything with small primers. The other is setup for only .45 with large primers. I tend to only switch calibers on the one for small primers only if I have 1000 or more cases needing to be filled. It doesn't take a lot of time to make the change. I just like being able to walk up to the press and load. I often only load ammo for 20 minutes to an hour at a time. I can check things before loading the first round and still produce 100 rounds without getting into a hurry in those 20 minutes. I don't have a case or bullet feeder so my production rates aren't as high as some others might be. Loading 300 rounds an hour is easy to do and more per hour can be done if needed.
The bottom line is you can start with just about any press. Speed will cost you money for both the press and components. Not everyone needs the speed of the fastest or faster presses. If you are on a budget figure in the cost of components as well. It is not a great feeling when you have finally gotten your new press and have to wait to save up enough cash to by components to feed it to make your first rounds to shoot.