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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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5  
yes. "engineer" – sibbaldiopsis Apr 27 '11 at 23:04

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

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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This may not fit perfectly in all situations, but if you'll take an adjective, I'd say either overconfident, naïve, or arrogant, depending on the situation. These are all (slightly) derogatory/pejorative, to varying degrees.

overconfident, adj – too confident

This can be used to describe someone's decision-making process in a given instance ("We didn't consider that there might be copyright-issues to navigate before we could start... we were overconfident...") or of a person in general ("Jason is just always overconfident").

Of the words I'm suggesting in this answer, this one is the most general, and probably the least insulting, as it simply carries the meaning that someone isn't putting the clues together about how difficult something is.

This word carries no implication as to why someone is not seeing a challenge clearly. My other two suggestions have more of a flavor as to the reason that someone underestimates.

Next up:

naïve, adj – having or showing a lack of experience, judgment, or information; credulous

This is a less-direct way of saying that someone tends to underestimate a situation, but it still carries the implication you want, because of the general tendency of people with little experience to overcommit, and fail to recognize hidden pitfalls in advance.

"Naïve" can also be used to mean that someone is simply acting inexperienced; that is, someone with some level of experience is simply not recognizing certain factors which signal that a task might be a struggle.

For instance: an architect of several years' experience needs to negotiate with property-owners to secure a build-site. The architect can design the building just fine, but if they falsely believe that the negotiations will go over quickly and without any compromises, you might call this naïve.

Finally, we have:

arrogant, adj – making claims or pretensions to superior importance or rights; overbearingly assuming; insolently proud

This would be used if someone is overconfident but not naïve. That is, they should have sufficient experience to know better, and they generally understand that the task at hand would be hard for other people to accomplish, but not for them personally; ego clouds their judgement.

It's not uncommon for someone who thinks too much of themselves (or in some cases their team or equipment or some combination) to think very little of extrinsic challenges. Saying this of a person immediately implies they may be prone to fail at properly assessing challenges or adversaries because of their own ego.

This is probably the least-pleasant thing to say of someone – not only because it derides their personal character but also because arrogance is generally not something that is transient, unlike overconfidence (which can be strictly situational), or to a lesser degree naïveté (which can go away after a person has the right experiences to learn a given lesson).

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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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Welcome to Cloud Cuckoo Land!

From the ODO:

cloud cuckoo land

[mass noun]

A state of absurdly over-optimistic fantasy: anyone who believes that the Bill will be effective is living in cloud cuckoo land

More example sentences:

There will be no going back to year zero of this process - and anyone who thinks we can go back is living in cloud cuckoo land.

We have made it clear before that politicians who promise to abolish testing and assessment are living in cloud cuckoo land.

They are living in cloud cuckoo land if they think they can transform the ugly concrete monstrosity into desirable homes.

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