Unused Serial Output Pin -- I may be having a problem!

gmcmurry:
Everything is bypassed with .1 uf but I don't always show them on the schematic.

The datasheet indicates a 1 µF bypass capacitor at pin 16 / Vcc. Your schematic indicates a .1 (no units) capacitor.

What have you actually used?

gmcmurry:
Should I need the 220R between the Arduino and the MAX232?

I suspect any such external resistor is meant to protect both sides from a software mistake. For example, using RX on the processor to drive an LED which would create a short-circuit through both chips. That seems unlikely to be a problem for you.

How is it powered? The datasheet has a somewhat tight supply range (4.5 V to 5.5 V). Good USB power can reach either of those limits. Poor USB power can exceed them.