WhiteTower: depends on the distribution of your opponent .. if he has holes in his home then he is likely to have some moves in which he cant bear off .. so you might still have a chance

it also depends if you have a nice block in your own home, if you dont have that .. then dont leave both pieces there

it also depends if its a cube game or not .. with a cube game you might want to make sure you wont be (back)gammoned

it also depends on the match score .. when you are far behind you might want to take some more risks .. although i am not sure about that one

i most often move only 1 piece out and leave the other there to be caught by my opponent