From what I understand, the traveler effects your lower telltales and the main sheet effects your upper telltales. With the first scenario I would think traveling out until that back ones flow would work, but that doesn't make sense though if you're going upwind.

Maybe try to head upwind a little more and see if the back starts to flow, and then if the the top starts to luff, sheet in harder? Do you have telltales on the leech? How were they flowing?

I'm new to this as well, but these are just some of my thoughts.