When is a bird in the hand worth two in the bush?

The answer depends on a willingness to take a risk. Whether you settle for something certain, or gamble on getting more, will often depend on what you have, what you need, and what you want.

The answer would be

YES. A bird in the hand is definitely worth two in the bush, if you need a bird.

NO. If getting two means you don't have to get one tomorrow. In this simple example: if you found you could get two, and in more than half of your tries, then in the long run, getting two sometimes, and none other times, would be better than always getting just one.

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Yes, be happy with what you have. Sometimes going after what seems to be a better deal will leave you with nothing but a hand full of bird poop.