cross on to cross shore wind.
Has to be cross-on relative to the wave direction to ride back "upwind". The reason you prefer upwind is because you ride a TT. I think it is more difficult to ride down the line on a TT than a directional board. You need plenty of turns to keep the tension on, especially if it is cross-on and winds are light.
It might be harder to go DTL on a twintip but a standard twintip has problems going up the line as well. I use both the Mako 150 and strapless low and mid volume directionals and the Mako doesn't have the float to power deep turns up the face unless the wind is just right (slightly more onshore). The directional has the advantage when you've shot too far off the face to turn hard back up it because you can put the kite high for a moment, slow down and let the wave catch you and use the wave power to get your speed back.