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and lastly, do you ever cash out while in the red? when things go bad, do you sometimes take out less than your initial deposit, thinking, "it's better than nothing"?
Yes, actually I have found myself in this situation many times after suffering a bad streak of losses while playing dices or blackjack. I initially started with a modest amount or percentage of my budget and then I start I lose all of it rather quickly. There is when I decide it is time just to let go those losses and log out, calling it a day.
On the other hand, when I have a good luck streak, I believe it would be good enough to cash out when one has already reached a 1,5x multiplier on one's initial deposit. It is not something which will make you rich, but definitely enough to buy something nice and say you got something out of your gambling session.