Seeing as the loop send should be a low impedance line level signal, then you should be able to drive a good bit of cable with little to no loss as long as it's quality cabling.
I run all of this (left and right, not the Peebee in the middle)...
With no appreciable signal degradation.
I worry much more about tone suck before my amp than I do in the loop. Also, I find most tone loss as far as fx loops are concerned comes from one of the following...
1. Not matching signal levels as close to unity gain as possible
2. Too much compression caused by high gain tubes in the loop send and return slots (I prefer old American 5751's, GE, Phillips, JAN or Military tubes are fine) etc... Cuts back on excess compression, improves clarity and dynamic range, & reduces noise. (see also 1).
Yeah, it's the 50' in front of the amp I'd worry about, and not the 50' after the loop. I use Canare GS6 and George L's in front of my amp, and use the Rocktron Loop 8 to switch all my "before amp" pedals out of the signal path when not in use.
I've got almost 30' of low capacitance cable in front of the Mesa (15'+ between board and amp input, and 12'+ between guitar and board). The fx send and return between the Mesa & Loop 8 is another 18'+ each way, and the send to the other stereo amp's return is 18'+. So on either side I've got 66' of cable between the guitar input and each amplifier's fx return. That doesn't include the cabling between my pedals and the pedal switcher, so at times maybe add anywhere between as little as 6" to as much as 4' more cable.