Hey, I was just wondering how much this affects my tone when I play live. I find it hard to tell at home because I can't turn it up that loud.

I have 4 pedals between my guitar and amp, on an Orange Rocker 30. No effects loop unfortunately. Is this what's messing up my tone when I turn it up?

I know nothing of the sort, but what pedals do you have? If it's boss they dont have true bypass so its probably the pedals.

Ibanez RG350M
Peavey 6505+112

Boss CS-1
EHX Big Muff Pi
EHX Small Clone
KORG Pitchblack
Depends on the fact that they're true bypass. EVEN when turned off, they affect your tone, unless there is an exceptionally good buffer.
Also, see if your pedals are digital or analog. Digital pedals convert analog circuit signal to digital algorithms, making the natural tone tarnished and irretrievable, usually.
Carvin TL60
Ibanez RG370DXL
TheSyle Velcro Fuzz
Line 6 HD500
Peavey Vypyr 120 Tube

Close your eyes, shut out the world, and you will understand. Post-rock/shoegaze/ambient.

Blue Skies and Paign

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yeah, and the length of the cabling before your amp will make a difference too.
unless you've got active pickups.
Are they all true bypass?
If yes you'll want a buffer somewhere in your chain, if not then maybe one of your pedals has a bad buffer and is sucking your tone.