There are so many variables, it really is hard to know how to hit the right points with anybody. I'm sure there's ultimately some sort of data correlation that could be produced about what, on average, attracts certain types of employers. I don't think it translates well to individuals, though -- there's too much to know in the larger job market. Unless you have a laser-focused intent on one position in one company in one industry, it's pretty much a scattershot.
In the media company I now work for, my manager is pseudo-technical. He had an engineer sit in on the interview for any technicals. Outside of the side projects, one of the major points I scored with them was that I knew anything at all about Adobe DPS -- and I hardly knew a thing. Vague private interest in how modern publishing was being handled translated into a position in a company that does it. Downloading an outdated demo at one point to play around for an hour or so translated into talking points. The engineer relied more on general technical knowledge for his approval, and seemed to avoid the typical "programmer interview" questions.
So! I guess my point is that people shouldn't rule out play as valid experience! Isn't that how most of us started on this kind of work to begin with?
Do things, build things, break things (and then fix them)!