badgersSometimes in gully & many other maps, process for example I'm watching computer & a soldier kills me with splash damage easily, when I'm holding just out of the health packs range. Or in gully: I try to watch flank; but get too aggressive and soldiers pick me w/ a scout. I guess sometimes I get baited, but that is not entirely the case.
The good news is this problem is very easy to fix. From what you have described it seems like you and your roamer just aren't synced up well enough to play off of each other's damage and positioning.
Something very important for you to personally do is consciously be the bait that gets your roamer to output damage on the other team. It could be that either you or your roamer have a w+m1 problem, but honestly it doesn't matter who "the problem" is. The blame game won't fix this situation. The only solution for your flank's situation is for you and your roamer to actively keep track of each other's positioning.
If you don't see your roamer around then it should be an immediate red flag for you to not try to make plays, because most likely you're going to end up getting baited to death. If he doesn't see you around it should be an immediate red flag in his mind to wait until you're there to help. You and your roamer need to have an understanding that you need to be patient with your positioning until you are both in a good position to trade damage with the enemy flank.
It's really really simple once you practice it. I hope that made sense and helps you and your flank out. :)