I would say he should keep his toes wet… dabble with some small pet project, or something to keep his skills sharp. Or even learn a new tech. Just don't let your skills go dull, while you're living it up… but definitely enjoy the fruits of your labor!
Take a break, do little projects & kick around for a bit, and contact interesting-looking companies about jobs occasionally... but don't jump for anything serious until you feel genuinely excited about it.
Give that part of your brain/spirit time to recover. As much time as it really needs, if you can afford it.
All that said, if you're interested into a side project that falls squarely into your line of experience, I have an interactive music site that needs rethinking and that's getting more & more requests on UserVoice for iPhone/iPad apps; I also have my own brainstorming on how to transform it into something really useful:
