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).
Someone with ten years' experience shouldn't be applying for the same jack-of-all trades positions as fresh grads. He should be applying for positions where a few years experience keeping a revenue-generating site going is a minimum requirement.
Well there are two possibilities. You can work a job for 10 years but if you learned the duties of the job in 6 months and just went on auto-pilot for the next 9.5 you're gonna be in the same boat as new grads. On the other hand if you learned and advanced in your field over those 10 years, then yes you will be looking for higher level jobs than entry-level code monkey jobs.
I had two "jack of all of all trades, master of none" for a cumulative of 5 years out of college.
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.