I’ll take just one of your examples and show real world conditions - a bicycle.
First, you have road touring bikes. These are made for flat surfaces with little to moderate roughness, aka roads. They use tires that are small and high pressure, so they will roll easily and not grip the road as much.
Then you have mountain or trail bikes. These use similar sized rims, but the tires are big and balloony, and have big treads for gripping.
Both are very similar vehicles with different requirements. The wheel diameter (rim size) is determined more by the size of the rider, i.e. the frame of the bike big enough to allow legs to pedal it, etc. The tires are changed.
This points out a question: do you just mean tire size (thin vs. thick, narrow vs. wide), or hub size (diameter of the rim), or both?
For rim/hub size on a bicycle, you have constraints from functionality. As I said, they have to be large enough to allow the pedals to revolve without scraping the ground, and give some clearance in the process. Wheel size could be smaller than conventional and still use the same frame size. Other factors include ability to climb over obstacles (i.e. curbs, rocks, etc), and rolling energy. Note how most bikes use gearing to allow different ratios of turning between the pedal cycling and tire rotations. This allows you to adjust for the same amount of effort in pedaling to match different terrain requirements that take different levels of energy: slope, wind resistance, roughness, etc. Different wheel sizes would require different gearing.
Think about the physics of rotation. Velocity at the rim is proportional to the radius. A larger wheel size has a faster rim velocity for the same angular rate (i.e. rotation speed). Think about it - you turn the same angle, say 180 deg. If r= 6 in, the corresponding circumference (i.e. distance traveled) is less than if the radius is 12 in. The distance traveled is bigger, but the time to travel is the same. v = d/t = wr/t
w = omega, angular rate
d = distance
t = time
v = velocity
r = radius
So if you have smaller wheels on your bicycle, you will travel at a slower speed for the same gearing and pedal speed.
To relate this to trailer wheels, which are not geared. The smaller your wheel diameter, the faster the wheel will rotate at a given vehicle speed. The wheel has to go around more for the same travel distance. Same vehicle speed or linear speed means same distance traveled in the same amount of time, ergo the wheel goes around more.