Oak is a tough cookie to get used to playing. I had the advantage of playing him a lot early on when everyone was just learning the game. You're probably going to have a tougher time with it when playing against experienced players.
Oak is an excellent general
Oak is an excellent assasin
Oak is excellent as a gen/assassin hybrid
The trick is knowing how to pace yourself in early encounters. Don't expect to wrack up a ton of kills pre-level 5. As in that movie above, learn to love the term Tactical retreat.
Speed (swift ankelts + boots of speed at level 1) is a great way to start for a more assassin oriented build
Mana helm + teleport scroll + heal potion is another good starting combo for a more general or hybrid oriented build (plus swift anklets favor item)
Learn how your skills compliment one another. Every skill Oak has is useful on its own, but when you combine them effectively they make for deadly combos.
Here are a couple of examples -
Using penitence to open a fight, get close to the DG (away from towers) and pop surge of faith. Follow with another penitence and start chasing the enemy down. your penitence slows + debuffs, while your surge of faith increases your attack speed. As he retreats (and he will) chase until just before you hit the towers. If you almost have him down, hit shield just before you get in tower range, finish him off and make a speedy retreat.
If you decide to take raise dead early on, make sure you put at least one rank into soul power and focus on always having at least 2 ward flags up. This ensures your attack power is maximized by the added spirits (I think its +40 weapon power, +20 for every 3 spirits you have up). Combine this with penitence and lure the enemy away from their defenses. If you mock like running away, while at the same time sending your spirits to attack the enemy DG, they will generally follow you. As you pull him far enough away, hit with penitence to slow him down, turn around and start wacking.. The slow movement speed + your spirits chopping away will often catch and enemy DG by suprise and you can finish him off before he can retreat to his towers.
The nice thing about Oaks skill trees is that you can create amazing hybrids that pretty much allow you to max out your most important skills while still being able to round your character out with the rest of the skills in the tree.
In games that I hit 20 I usually have something that looks like this:
Penitence maxed
Surge of Faith Maxed
Spirits to level 4
Shield to level 4
Divine justice to level 4
Soul power at level 1
The only skills I don't often take are Last Stand (or whatever that one where you turn invuln after you die) and morale, although I sometimes take morale if I've got all my level 4 idols and a high rank of Raise Dead before level 10. Maxing out your Morale will help a lot in the late game if you're a minion oriented player. Otherwise they tend to get one shotted by enemy AOE's.