Is this like some sears social media campaign? I'd say if you are a complete newby to avoid sears/craftsman, that place is a mess. Better off going with a brand that is on the up and up and logically organized and more predictable. This will help you avoid confusion

.
Drive sizes are measured by the amount of tool steel in the square drive. The cross section is the amount of metal (or the size x size = size squared)
36mm(sq) = 6x6 (6mm=1/4 drive)
100mm(sq) = 10x10 (10mm=3/8 drive)
169mm(sq) = 13x13 (13mm=1/2 drive)
I've rounded the numbers but ya'll can see the gist of the math.
For practical use, 1/4 drive is for fasteners up to 30nm in torque rating, 3/8 drive for values up to 100NM, and 1/2 drive for values up to 200 or so. The limits for rated (DIN) strength is probably about twice those figures. Again just very loose estimates, and actual tools may be built much stronger.
Usually where the sizes overlapp, the dimenions of the sockets are not equal. They will typically use thinner walls on 1/4 s 1/2 because the bigger drive sizes are stronger so the sockets are stronger. The lighter and smaller tools will then fit in different places.
In modern applications, aerodynamics and economics have led to very confined workspaces. Basically manufactures shoud the motor with a windscreen, and try to make that windscreen as small as possible. This means that the engine is tightly wrapped, and the enclosed space makes tools that fit in small spaces more important in certain applications.
airplane and motorcyles are a couple examples where this is even more significant, because they both tend to be weight sensitive. so again smaller hardware, more confined spaces, ligher weight but stronger fasteners, packed more closely, etc and generally smaller tools are used as a result.
So the sizes you need depend on the fasteners you need to work on, and also there arrangement. Some people work with 1/4+1/2, and others build up around 3/8 with a springkling of other stuff for the extremes. It really depends on what you work on. Overall the trend is to make the smaller drives more standard, whereas the original standard drive was 1/2, today for many people 3/8 or 1/4 is the go to size for many things. Lastly, I woud add that corrosion and cleanliness come into play. Precision fasteners vs Messed up fasteners will likely best be served with drives more suited toward the extremes.