Max Current to Draw from 5V Pin Safely?

Since you're using the barrel jack for power, if you need more you can draw it from the VIn pin. When the arduino is powered via the jack, VIn gives you a direct connection to your supply and bypasses the voltage regulator. Just don't forget to connect it to a regulator of your own to drop it down to 5v. I believe you can go as far as 1A before you need to start worrying about overheating things.