Best course of action IMHO: First make sure you're using the BEST cables - all cables - this is the biggest mistake I see!! I prefer Evidence Audio cables for everything!! Second, I got caught up in all the botique pedals in my search for tone, particularly with OD pedals, what I learned later, I was just searching all along for that Dumble like OD tone - forget as much as possible pedals and save the money and get a Ceriatone (if cost is an issue) or a Two Rock, etc...whatever wets your whistle - don't buy pedals to emualte the amp you don't have is what I suggest.
True Bypass is better IMO than non true bypass, but once you start with the first pedal in front of amp, the probelm begins and amplifies the more pedals you use - too much hose in front of amp IMO...you can't have your cake and it eat it, if you want pedals, understand that tone loss will happen. Try if you can to first use two amps that compliment each other, via Marshall and Two Rock rather then using pedals to find the tone with inferior amps, guitars and cables.
Bottom line: Best cables, great guitars set-up professionally, great amps and limited use of pedals IMHO.
Last Note: Everyday I find myself losing pedals and using a pick less and less - it's like a graduation of sorts, for me at least. So much can be accomplished with pick/finger attack to create your own signature tone. I'm about to sell probably at least $1K or more in pedals to buy a second quality amp and just use a Katana and or maybe my Providence SOV-2 OD or Dumkudo OD pedal for some extra boost when needed..ok maybe keep my T-Rex Replica delay....then done for me.
Wow...sorry for the rant...off to a glass of Red Wine
TF