I am finding it hard to make much of an outdoor encounter in RTL. In fact sometimes I feel its a waste of time to setup the board. The 1 or 2 damage I seem able to deal out pales in comparison to the cash they make off of it. Is this supposed to be a player cash grab kinda situation or am I doing something totally wrong?

Tips or strategies anyone?

It all depends what you draw. Some of our encounters I am lucky to get a hit in. Sometimes it is different and I am able to do ok, sometimes even kill a character.

The presence of trees really make all encounters different from normal dungeons.

Don't start too close to the heros, Since you gain 4 threat a turn, making them come to you is in your best interest. If you'd like to do good in encounters, upgrade beasts, They are the most common creatures on the overland map, and soaring creatures are brutal.

Other than that, just bide your time until you draw box canyon. Then you'll have your revenge.