It is certainly possible for the outside, leeward telltale to not stream properly while the inside one is, and that is when the jib is overtrimmed, or stalled. That is probably one of the most common beginner mistakes, and a definite speed robber. It is so important to avoid this, if you are doing any racing at all, that I would always insist on having telltale windows. Sure, you can make out the leeward telltales when the jib is backlit as in jssailem's picture, but they are impossible to see when the sun is shining on the near side of the sail.
The only downside to windows is the slight additional cost, but I feel they are well worth it.