I can't answer half of your questions but I can answer the fuzz face with a boost pedal. My answer is yes, I hated my fuzz face by itself and to be honest through a dirty amp really didn't sound good to me because I hate the sound of distoriton on top of distortion. It sounded like it was farting so I had to use mine clean. When I was ready for a lead I had a boss blues driver at the time and it worked perfectly when setup like a clean boost. The tone control all the way up really cleaned up the mud from the tone and the level really pushed the transistors hard so it really cut through.
I think if it was me I would run your chain like this: Guitar, wah, Tube screamer, Power Stacker (you could switch the tube screamer and powerstack around depends on what you want. Tube Screamer after the the power stack with make the volume of the stacker louder, before will make the distortion push harder but not a big volume change.) Then the fuzz face after that. It could be argued both ways if the fuzz should be the last distortion pedal or the first pedal I personally would leave it out. The pickle vibe should always be after the distortion, if you do it before it will sound amplified by the distortion pedals and the effect will swell more then its sposed to do. if you don't use the Big Shot I would make the delay last. I don't know how the Big shot works so I can't help you, but if you can tie that in as an effects loop I'd put the delay in the loop either by itself or with the pickle vibe. I don't think you should run any of your distortions or the wah in the loop, however I did do this once with a Luther DRive which is like a tube screamer. I had my amp distortion as high as it could go and to boost my solos it wouldn't give me a volume boost where I wanted it. So I stuck it in the effects loop which bypasses the preamp and made my amp scream. The people in the front row at this party was not happy but after a few songs I backed off the level and was fine. I hope this helped.
