I generally buy used for the reasons you mention and save a bundle, so longs as I don"t expect new and shiny. I just bought an 8" rockwell jointer for $400, but I have to work at it to get the gibs out and I"ll have to rewire the switch. No biggie.
I think if you are running a casual shop (ie your groceries don"t depend on it) older used is your best deal. Otherwise you will have to ante up a lot of money for a General out of Canada or a Laguna Tools or another tool intended for commercial shops.
Its kinda like... tractors. Expect to work on "em. Expect the new ones to be less user-serviceable than the old ones, even though they are more pricey.