I wouldn't be so optimistic about the "jack of all trades" point. The problem there is that, as a generalist, that's one less leg up you'll have on new grads (who are also usually interviewing for generalist positions).
Life got considerably better as I started specializing towards a track of Front End Development. There's a huge gulf between being the guy who can write spaghetti JS and CSS to developer but its doable, although it was much easier 6 years ago when left the Jack-Of-All-Trades. I'd suggest picking a part of your skill set if you have extended downtime and trying to level up. Having a broad skillset won't hurt you, but not having anything technical will.