Should you buy tools for your contractor?

Any decent contractor should already have to tools he needs, or have factored them into the estimate. If a contractor starts asking you for new tools to do this or do that, I would be concerned that he didn't know what the job was when he bid for it. That would be like a mechanic asking you to buy him a ratchet because he never realized that a ratchet could be useful. But if you added on to the job after the initial estimate, and new tools are required for the new work you need done, then maybe you should either consider it an expense or bring in a second contractor to do that part of the job.