A simple, single FET buffer might be enough to prevent problems, but if you needed a "bypass level control" to match levels you could use something like this (the level control could be a trimmer inside the pedal to set and forget) -
From Beavis audio:

or there's a thread of them here:
http://www.diystompboxes.com/smfforum/index.php?topic=94578.0I think this is a situation where you're probably best to try it out as you've drawn it, and see if there's a problem. If there is, you have some options to try. A dual volume pot on the stereo loop returns is the simplest solution, but means you are permanently reducing the signal level going to the two amps (either with passive splitting in bypass, or reducing the output of the stereo loop when it's engaged). The buffer or buffer+booster option means raising the bypass output to match the stereo loop level, but also means permanently buffering the bypass signal, which you might consider to defeat the whole point of your true bypass strip...