Manufacturing tolerances, differing wear and tear, after connecting through Y leads, they might not be getting the same voltage.
Signal timing as such won't be affected, the signal travels at the speed of light, and it takes a lot of slowing down to change the pulse length with any significance. A long led "might introduce some extra capacitance in the signal wire that "might" have the effect of delaying the start and/or finish times of the control pulses by a microsecond or so at the receiving end.
Digital is a marketing word that gets slung around quite indiscriminately by sales and marketing, who generally haven't a clue what it means.
I have 27MHz radios with "digital" on the label, alongside "AM". That just means that it contains some digital logic circuits, even if they are not performing any actual digital function. The PWM signal that is involved somewhere along the line with just about every radio control system is as analog as you get, even if it is switching on and off like something digital. The pulse length is analog, honest.
Just how digital are digital servos? I don't know, but they respond to the exact same pulse length signal (length is the analog bit) as everything else that plugs into a radio.
An analog servo converts that pulse length into a value which is compared to that being generated by the position sensor, and seeks to make them equal by driving the DC motor using another bit of PWM. The nearer equal, the slower the motor, this to prevent overshoot, because motors have inertia.
A digital servo must respond to the same, analog coded, signal. It "might" convert the pulse length into a number to be compared with a number derived from the position sensor, or do that job just like an analog one. When driving its motor, it "might" fire the motor at full speed until it gets where it is going, and use a bit of brute force braking to stop it dead. A full digital one would do both, I suspect that "marketing" digital ones just do the latter. Advertisers are going to need to find a new word when really digital stuff arrives.