There's a bit of personal preference involved, but a good rule of thumb is to stop adding ink when it no longer soaks in immediately like you're watering a bone-dry houseplant. I know it's time to reink my pad when I really have to work to get coverage on the rubber so that there isn't a lot of white paper showing through the stamped image. Also, the edges of the ink pad will begin to pull up out of the plastic casing, presumably as the fibers shrink up from drying out.
I like to draw lines across the surface, first horizontally then vertically. This helps me to get good, even ink coverage. Depending on how dry your pad was to begin with, it will usually take roughly 1/4 or so of the bottle. It sometimes helps to close your ink pad and let it sit for a couple of hours before you use it again, so that the ink can soak all through the pad. Occasionally when I use a pad right after reinking the surface is a bit too juicy and the color comes out too dark.
__________________ Rachel
Proud SU! demo and Sci-Fi Geek!
My Stampin' Up! blog
"I'm a time traveler -- I point and laugh at archaeologists." 10th Doctor, "Silence in the Library"
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