#2
never enough pedals!
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#3
Anything you put in the signal path is going to affect the tone, but probably not significantly. Too many pedals will degrade the signal, and you will need a signal booster somewhere in the chain in order to bring it back up to full strength. More and more high-quality pedals have true bypass, so the tone-diminishing properties have been reduced. You can definitely overdo it with pedals, though. If your pedal board becomes too heavy to lift with one hand, you've probably got a problem.

If you use a lot of pedals, you can get a pedal controller to set up schemes where you use only certain pedals at one time and the others are removed from the signal chain. Carl Martin makes a very good one that lest you arrange for eight different schemes for your pedals:
http://www.carlmartin.com/product_octaswitch.htm