I am in central pa and here an auction would absolutely be the best option. around her the wood would only get 25 to 30% of what you would pay at a lumber mill. But the tools if they are true industrial quality will pull in 60+% of retail. In our area the amish and Mennonites love auctions and will pay very good money for quality used equipment. But I honestly know nothing about your market in boston. id try looking for a dedicated woodworking site with a classified section you might have good luck there. But site like that generally only industrial quality stuff sells well not homeowner grade stuff like craftsman unless it is raelly old craftsman when it was still quality equipment.