I've just been reading the spec for an AD converter which may be usefull:
Analog transmitter output, 16-bit, scalable and isolated. User selectable 4-20 mA, 0-20 mA or 0-10V levels. ... The supply can drive 20 mA into a 500 ohm (or lower) load for 10V compliance, or 10V into 5K ohm (or higher) load for 2 mA compliance.
The important point is that the output is conditional on the load resistance. (and the "or lower" bit probably means not less than 200 - 300 ohms, or the device will start malfunctioning)
I would have thought the AD DA solution would have been the best but at 300m the major problem would be pickup on the signal cable. Is it an electrically noisy environment? Intuitivley I would go for the best screened cable I could get and rout it well away from any other electrical cable and preferably in the ground!