As others have said I think it depends a lot on where you usually skate, as in what the surface is like.
If you are riding a surface that wears down wheels quickly, getting a bigger size really does make a difference as they will wear down nicely in the Classic shape (which I prefer) but if you are skating smooth glass like surfaces, then getting a wheel in pretty much the exact size you want is best, as they hardly wear down at all on that new skatepark or similar surface for the places I have been.
Ideally, I get a bigger - 55, 56 or 58 mm - Classic shape wheel and skate places I know will wear down the wheels more quickly, so then when they are about 53 to 54 mm, the right size for what I like, I can then use them on the glass smooth parks, or my ramp at home, where they hardly wear down much at all.
This would be a good idea if that is how it worked all the time, but I do have a lot of nicely worn down wheels as trade ins from others as well, including mostly 50 to 52 mm sizes that were 54 mm Conical Full wheels when new, that I round off the sharp edges on, which also works really well for me when I skate smaller stuff, as well as others who like a smaller wider wheel for street tech type stuff too.
Some people love the chunky look and feel of bigger Conical Full wheels, but anything over 54 or 55 mm is not a wheel I like to skate for anything other than just going fast, which is fine for the 55, 56 and 58 mm Conical Full wheels I still have too.
More people skate the 54 mm Conical Full and quite a few skate the 53 mm size that I know, more as a single size and shape all rounder for everything, which makes sense.
Lastly the Classic Full (just a wider profile of the Classic shape) is my perfect go to in 56 mm when new, but besides that wheel being virtually extinct unless you stocked up when they were around, I just don't find myself skating a whole lot of bigger transition the way I used to, so I don't even think I will go through the half a dozen sets I have now anyway, as I am skating a lot more on the other smaller wheels as shown above.