I understand it as two devices in series where you can read the current. Not as two sensors in series on the same twisted pair, right?
It is a matter on how many volts are available at the source, if you add all the loads in the path at the max current. With Gunnar's exemple, if the total resistive load is at 500 ohms, and the source has 12 volts, there will be only two volts of play for all active devices and linearity problems will occur, as some devices may start saturating at their extremes. Some devices also use zeners to in the current loop in order to feed the sensor dirently from the loop. There is an additional voltage requirement for such devices.
Find what the requirements are for your input devices and what is the voltage available at the 4-20mA source.
As a corollary, once you have these numbers, you can choose to increase the available voltage instead of using a thicker gage wire. One mile of wire isn't cheap. It depends on what devices you have.