The question of how to initiate, for a wheel on a frictionless surface, rolling motion identical to what could occur on a frictionful surface, is interesting. Most pushes on a part of the wheel, or a stiff, weightless handle attached to it, would initiate a translating, rotating motion that did not match any frictionful rolling pattern. It is necessary for the wheel's angular velocity ##\omega## to relate to the linear velocity ##v## of the wheel's centre by the equation ##v=\omega R##, where ##R## is the radius of the wheel. For the motion to always match a rolling motion, it is necessary that ##\dot v=\dot\omega R## at all times.
On my calcs, if a force is applied at angle ##\alpha## counter-clockwise of vertical, at polar coordinates ##(r,\theta)## relative to the axle (with ##\theta## being measured as angle to counter-clockwise of the vertical), the following equation must be satisfied
$$I\sin\alpha = rRm\cos(\alpha-\theta)$$
where ##I## and ##m## are the moment of inertia and mass of the wheel.
If we are applying the force to a handle that is at a fixed distance ##r## from the axle, we would need to continuously vary the angle ##\alpha## of our push in order to maintain the motion as rolling-like. This gives ##\alpha## as a function of ##\theta##.
Alternatively, if we fix the direction of the applied force as always horizontal, the radius at which it must be applied will vary with ##\theta##, being at a minimum when it is applied at a point above the axle (##\theta=0##) and increasing without limit as ##\theta\to\pi/2##.
The size of the force makes no difference. It cancels out of all the equations.