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Does there exist a single word, either an adjective or a noun, that effectively describes an individual who habitually underestimates things—e.g., cost, time required, complexity?

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yes. "engineer" –  sibbaldiopsis Apr 27 '11 at 23:04
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3 Answers 3

If you really and truly want to make do with just a single word alone, you are going to have to go with a word like a chronic underestimater or underestimator, a misjudger or even a low-baller.

So it seems that they are perpetually falling short of the mark in their subaccurate assessments. Given that, I think what you are really looking for is someone who is actually overestimating not underestimating something. They are overestimating their own abilities at getting things done.

When this is a chronic characteristic, what you have here is someone subject to the Dunning–Kruger effect:

The Dunning–Kruger effect is a cognitive bias in which unskilled individuals suffer from illusory superiority, mistakenly rating their ability much higher than is accurate. This bias is attributed to a metacognitive inability of the unskilled to recognize their ineptitude.

Someone who is actually competent will learn from their previous mistakes, and make allowances for all this in the future. But those of lesser competence are also less competent at assessing their own competence, and so always think they will do more in less time — and do a better job at it, too.

So I suppose you could them a victim of the Dunning-Kruger effect, or just a Dunning-Krugerite for short. I know I’ve certainly used the term with people whom I know are certain to understand me, but it is not in common parlance.

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How about an optimist:

someone who has an inclination to put the most favorable construction upon actions and events or to anticipate the best possible outcome

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+1. This was my first thought. –  kitukwfyer Apr 27 '11 at 18:48
    
Hm. I don't know if that necessarily indicates underestimation. For example, an optimist might actually overestimate how trustworthy people are. What do you think? –  LucasTizma Apr 27 '11 at 18:50
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@LucasTizma Well no, it is what came to mind from your examples, which are all things that an optimist would underestimate. –  z7sg Ѫ Apr 27 '11 at 18:54
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Maybe you'd refer to that person as "Panglossian", or "a Dr. Pangloss", after the highly optimistic character from Voltaire's Candide.

Or you might say she was "Polyannaish" or "a Polyanna", after the eponymous character from Eleanor H. Porter's famous novel Polyanna.

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