I have had the opportunity to work for SoundStage here. They are responsible for Lakewood Amphitheater. I can assure you I have never seen a guitar setup without a rack of effects and drawers of pedals. I own lots of pedals, but not many cheap ones. The paisley drive is a wonderful pedal, but it does not perform well if certain pedals are in front. For instance, my keeley compressor in front of it makes too much noise, but if I put a dynacomp or a Analogman Comprosser it works quietly. I have found the sparkle drive superior to the Ibanez tube screamer.
So you asked about setup of grab and go. The amp has to have a tube overdrive which is switchable with my foot. For grab and go at the amp input I have first a compressor, then an overdrive. I have a paisley, and a sparkle drive and the last thing in the chain is a BB+ xotic. The BB+ had the feel of an amp and will sustain for days. In the loop the first thing is a Boss GE7 which had been modified to reduce noise. I have 2 different delays, one a Wampler Tape Echo and a MXR carbon comp for slapback then the THC chorus to a phaser MXR script adapted with a 9v input, from mid seventies and for reverb I have a verbzilla. Turn up a 15 watt amp wide open, but it has to have an additional gain stage (tube).
Does it sound like my 73 marshall running 8, 10. No, never will. But to get this rig where the guitar will play with only my chording hand it is too loud for clubs these days. The 70's and 80's are gone. I can get the amp to the volume where it will feedback without being too loud. I think this is the secret and then use pedals to accentuate tone. If you cannot get the amp screaming, then you are completely relying on pedals for tone and overdrive. Might as well just take pedals and go into the Sound System. I know a local band that does just that and it sounds as you say plastic.
I can tell you that when someone mentions Grab-and-Go, I think of having to play most anything. I may be going to play classic rock, 80's rock, Country, blues and even some pop.
Playing a gig is a different story all together. I know the Line 6 stuff is considered by some to be a joke, but I have a rack unit as well as a Rocktron Voodo Valve and Alesis midiverb. I have many different pedals and if I carry all of them the board is sidestage with only a controller. Pedal board is about 5 foot by 2 foot.
Effects are necessary, but overdrive is a different animal. To get the amp really singing, turn it up. Boosters are my friend as I seem to get a better amp tone if I hit the front hard. If I am the only geetar player I always use humbuckers in the way of a Les Paul or a 335. I know SRV used a strat, but I just am not a fan of that tone.

I do a lot of Country gigs and this is simple. If it is big place it is a fender twin with delay and a telecaster if there are 2 guitar players. If only me, Les Paul. It is a style and you cannot just buy a telecaster and it magically appears. Gotta use you fingers.
Also, high output pickups have never worked for me. I use classic 57's or PAF, nothing else. It the tele it is only noisy broadcaster pups.
Sorry for the loooooong post.