I suppose it depends on where you live. Maybe more common than I realize.You find wood heat odd?
As to the actual point of this thread, this gig is far enough out that they should be able to find a sub. I don't see how the finances work out at all or what made him think this was a good deal. A top wedding band in downtown Chicago, for example, would probably make at least $13,000-15,000 on NYE, especially considering the other potential NYE gigs they'd be giving up for a wedding.
More importantly, you have three kids, an ailing parent, and this is not your primary source of income. He's in a different stage of life without any of those things. You're bound to have mismatches and this probably won't be the last time.