Obviously this is somewhat subjective based on all of the pedals you have, but at what point do you realize/does it become obvious that your pedals are killing the tone of your amp? And if you reach that point, what pedals to you recommend to help offset this? The same goes for pedal boards too...as I'm currently going through my internal debate of digital effects vs pedals. Do they tend to kill amp tone as well and how do you recommend offsetting it?
good pedals don't kill an amp's tone.

a bunch of crappy ones strung together do.

the weakest link in the entire chain causes the most harm to your tone, including you.
I wondered why the frisbee was getting bigger, then it hit me.
i've gone through trends of steadily plugging in more and more pedals before deciding to go for something different by plugging straight into the amp. I'm usually amazed by how different the tone is. sometimes the tone improves, sometimes it doesn't. i definitely swing both ways on the issue.

I'd recommend steering clear of digital effects when you can. if a pedal isn't making the tone you like, stop using the pedal, don't offset the tone loss with another pedal. though, i do like the sound of a compressor placed before (NOT AFTER, it'll sound like crap) a distortion pedal and i've heard some interesting things from EQ pedals (Dimebag swore by his EQ pedal, i believe)

edit: from the threadstarter's first post, it seems like he's looking at one of these big multi-effect pedalboards. if you get one (a line 6, for instance) and it has amp emulation or whatever, it might be able to plug into a computer, and you could record with it. which is fun as ****. most of Dethklok's albums were recorded that way, with a line 6 pod. though Dethklok's tone sucks 90% of the time on their albums, in my opinion. I'll shut up before I rant any longer
dont take any guff from these bastards man

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Last edited by spiderjerusalem at Nov 20, 2011,
Are you referring to the whole true bypass vs buffered pedals issue here? Pedals shouldn't suck tone from your amp and if they do I would look at testing them individually to narrow it down to see if there is a problem there. If you are referring to the whole capacitance thing then Visual Sound make a good little device called the Pure Tone Buffer to eliminate capacitance.
If you're chaining a bunch of stomp boxes together at least invest in decent patch leads. As mentioned above, the weakest link in your chain will suck your tone. Steer clear of the multipacks of coloured, molded patch leads.

I did some house tech work for a venue last year and a band of kids came in. The pedalboard their lead guitarist had was chained using the aforementioned patches and he wondered why it was sound like 5hit and then promptly died. About 30 minutes before they hit the stage. I threw the lot away and had someone do a run to my place to grab my spares.
It's an opinion. It's subjective. And I'm right, anyway.
if you use fx properly they should enhance your tone not kill it. if you are using fx to cover up deficiencies then you are heading down the wrong road. many players new to fx heap them on which can kill your amps natural tone. often less is more.
I read an article on Premier Guitar a couple months ago, explaining that with the vast improvements that have been made allow higher end (certainly more expensive) multi and digital effects to give you analogue tone. I'd post the link but I can't find it right now... That being said, I swear by analogue FX. It was eye opening when I shifted my attention that way.

The other thing is that with digi FX, you have to set all your patches just the way you want, and tweak every little detail to get the sound you're looking for. With analogue, most of the pedals out there are plug and play. It lets you get down to what you're really wanting to do. Play your guitar.

Hope all this helps!