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Much thanks to everyone who replied! Here is a link to the column:

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http://www.omaha.com/living/evans-you-can-find-waldo-if-you-look-hard-enough/article_481877ee-8f1f-506d-9af3-8d3831516567.html

For me Waldo is way too associated with a dorky looking man in a red and white striped shirt to ever take seriously.

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Hmmm no, I think those names are popular because they're shorter versions of already known names. "Waldo" is just plain old Waldo.
Also "Milo" and "Arlo" both end with "lo", maybe that's a trend?

Yes, Waldo has a silly/dorky image to me. And a clunky/dusty feel as well. I grew up with "Where's Wally?" books, but I don't think they're as popular now as they were back in the '90s, so that association alone wouldn't put me off using Waldo/Wally if I was so inclined. On the other hand I find Walter sophisticated, refined, intelligent, strong and handsome.

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Arlo, Leo and Milo are "lighter" than Waldo. Not dorky, but more youthful/immature. I guess you could say they're "cool", although they're not my taste - they're better off on dogs/cats in my opinion!

I think Waldo is kind if cool and charming, I really like it!

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But I am not from the USA and here in Germany the books and TV show was called “Wo ist Walther?“.

Waldo is pretty geeky to me. I can't take it seriously, especially with the books. Leo, Milo, Arlo all have a '20s vibe to them that make them cool. Waldo has a 19th century feeling to it.

I adore Waldo! I would certainly consider using it, but I'm not fazed by most charges of unusability. I'm very familiar with the "Where's Waldo" series/phenomenon, but it wasn't integral to my childhood.

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For the record, I'm 26, and I was born and raised in the U.S.

Waldo sounds dorky to me, but because of my age I don't consider my opinion to be in any way indicative of what names are up-and-coming among those who are in their child-bearing years. It's a common phenomena that grandparents are appalled by the names of their grandchildren, due to changing tastes.

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I do think of "Where's Waldo?" Objectively speaking, I don't see why Waldo can't fit in with Leo, Milo, and Arlo.

Waldo definitely sounds silly and dorky. We didn't have Where's Waldo, although I have heard of that. We have Where's Wally and I think Wally is a similarly silly, dorky name.

It doesn't seem to have ever gotten very much use at all; I can't think of any famous Waldos except for Where's Waldo. That, to me, that being tied so tightly to one single character, is a huge strike against it right there. Also, it just sounds comical, like a big goofy dog who knocks things over just trying to get from one room to another.