Chris, you will probably get alot of answers to this question, here's what I do.
Below 40F, plug in for 2 hours before takeoff.
Below 20F, plug in for 3 hours before takeoff.
Below 10F, plug in for 4 hours before takeoff.
Below 0F, plug in all night.
Some members plug in all nite all the time, won't hurt anything but your electric bill. I use a HD duty timer and just set the timer to when I want it to go on and for how long. Another member reccommended always unplugging while the line is still hot as it may help prolong the life of the block heater. I'm not sure if it helps, but that's what I do.
As to the second question, I don't have the luxury of plugging in while at work. My truck sits 8-10 hours a day while I'm working, some of the winter days are well below 10F when I leave ( not this winter, so far

) and I've yet to see a problem starting, always allow the grid heaters (wait to start light) to activate before turning the key. If it's really cold and you haven't plugged in, cycle the grid heaters twice before start up as that will help.
Scott W.