Hello @magpie,
Your description of how the rudder works is not entirely accurate. I am not sure what you mean with the rudder lateral force will somehow force the airplanes sideways. Only a crosswind while landing can do that in extreme condition. In no wind condition or if the wind is straight down the runway you can land on a very slippery runway if you have enough distance to stop.
On many airfields circa 1940 the "runway" was so wide that you always could takeoff and land into the wind.
On tailwheel airplanes the danger zone on landing comes when the rudder is becoming ineffective as the airplane slows down, this is because you are losing your only aerodynamic directional control mean. You are two slow for the rudder and potentially too fast to use the brakes. Furthermore as the tail of the aircraft comes down the propeller, which is a gyroscope, pulls the aircraft to the right (to the left when raising the tail). Conventional landing gear configuration types are a piece of cake to land in comparaison.
As far as airliners there are no differences in terms of airplane handling single, double or triple boogies.
Maybe I did not understand your post. 😀