How old is he? Would he consider apprenticing/pivoting to electrical work? There's a real demand for electricians (with all the green tech being installed in Vermont). I still subcontract with an energy company and their in-house electrician was making beaucoup de $$$ installing solar panels and heat pumps. I doubt there's much to be made in furniture making. I had a friend who wanted to build and sell custom furniture, but there was little to no demand. He moved to California but didn't fare much better, so maybe the problem was his furniture? It's possible to get by as a carpenter, with a working spouse, but the real money is in contracting with a crew. I would NOT recommend Shackleton.