I pump until the bottom of the kettle is covered with trub. I know some goes into the fermenter but not a lot. Doesn't seem detrimental.
I drain, not pump, but otherwise same here. I eyeball the racking arm until I'm sucking trub and stop at that point. I ferment in a keg with a floating dip tube, so I don't have to worry about racking any trub into the serving keg.
FWIW, except for a dry hopped IPA, I wouldn't think twice about repitching from a beer that has some kettle trub in it. If it didn't hurt the first batch, its not going to hurt the second.