I do a lot of hiring and I don't see it as a big deal.
I do it myself, actually -- a small contracting job that doesn't really matter given everything else I've done, or something that doesn't fit into the 'narrative' I'm trying to sell the employer. I'm not trying to hide anything, but you only have a brief time to get the attention of the recruiter or hiring manager, and if your last job is interesting, the second-to-last doesn't really add anything, and the third-to-last is killer... then if that second-to-last job is short, I personally wouldn't hesitate to drop it. Hell, I cut my resume off at 5-6 years anyway, because a) it keeps my resume down to 2 pages, b) that's when I started my current career 'phase' and I don't need to sell people on a job I'm not applying for.
Then when someone like me comes and reads it, I get an uninterrupted flow of the good stuff. Also, it's important to note that 'someone like me' isn't looking at dates all that closely. If your resume lists "2008-09: Something awesome; 2010-present: something awesome", then I'm not spending any cycles at all thinking "Wait a second...what came in between those!?" I am only spending a few minutes per resume, looking for interesting experience, a good match for technologies, and that ineffible 'something' that great devs have. I'm looking at your LinkedIn profile and reading your blog...I'm not reconstructing your timeline in my head.
Once in a while I get someone with a 2+ year gap in their history...that makes me curious. But it's 'curious', not 'accusing'. I'll ask them what they were doing. "Oh, I was going to culinary school", or "I made enough money in the previous job to take a year and be a stay-at-home-dad, spent spare time learning technology X" or "I wanted to try being a professional musician a try, but it just didn't work out" are all things I've heard, and they were all fine answers. I've also heard "Yeah, I did some contracts, but they were pretty undistinguished and just took up space on my resume" and that was fine too, though I'd expect someone to get their career back on track in less than a couple years. "I was a meth-head, robbing gas stations" is a bad answer. :)
Also, for what it's worth, I don't really see multiple jobs in 5 years as a necessarily bad thing. 5 jobs in 5 years would make me wonder for sure, but where you are and what the tech industry is like can have a big effect on expectations -- 1-2 years is pretty much average in silicon valley these days. Seattle/Redmond has a little longer average, but someone with 2-3 jobs over 5 years is not a big deal. I'd ask why they left, but there are a lot of good answers to that question.
Finally, a caveat: This is just me. It's possible that you get someone who really does care very much and ymmv. But from my point of view, it's not a big deal.
-cw