[pzhon]

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What's a good way to gauge the amount to bet that you will get paid off?

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Think of what hands your opponent might have, and how much they would be willing to call with those hands.

Example 1:
I rivered a royal flush, out of position. The board had 4 to a flush, and it was paired. My opponent had the size of the pot left. How much should I bet? Answer: Very little. If my opponent has a full house, all of the money will go in anyway. If my opponent does not have a full house, he must be terrified of the board, and he has at best the third highest flush. The right amount to bet may be nothing to induce a bluff, or 1/5 of the pot or less to get a call from a weak flush or worse. At the table, I bet too much, and my opponent folded. He didn't have anything, though.

Example 2:
I had 98 in the big blind. Flop: J74r. Someone made a minimum bet, there was a call from late position, and I overcalled. Turn: 5, making a flush draw possible. Again, there was a minimum bet, a call, and I overcalled. River: 6, no flush possible, putting 4 to a straight on the board and giving me the nut straight. I didn't think anyone with a 3 would stay in, but anyone with an 8 would call any amount, but might not raise. I didn't think anyone had a decent hand on the turn or else they would have protected their hand from the flush draw. I open-pushed for 3 times the pot, and was called by the minbettor who had 87.

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Is there any time that taking down a pot w/o a showdown is bad?

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Of course. Some hands are worth more than the current size of the pot since you expect that you can get called by worse hands. However, if your opponents have nothing, and don't feel like bluffing, you can't get anything.