Re: I think it's time for a looper/router pedal
Check out Loopmaster
http://www.loop-master.com/
I have one, it greatly improves the tone, built like a tank, and reasonably priced. The bad part is it takes him up to 8 weeks to build you one, but IMO it's well worth the wait.
You shouldn't be completely true bypass though, you should put a decent pedal or buffer at the beginning and end of your chain- on mine I have a Boss TU-2 up front, then in the end and loop use a Boss NS-2, and use the looper on any pedals that aren't 100 % true bypass. You can turn the pedals off but they'll still act as a buffer, and Boss buffers are really good. That preserves tone the best.
Also, your tone is only as good as its weakest link. On your pedalboard, use high quality patch cables like George L, Lava or equivalent to connect the pedals.
If you're using a 4 cable method for the effects loop, consider a Pedalsnake. I got one, and using the Pedalsnake with Geoge L interconnects, and the 2 Boss pedals as buffers, Loopmaster, my rig is dead quiet, tone is bright, and really barely need the Noise Supressor on. I also use a Pedaltrain board. It feels like I took a foam blanket off my rig