Tips to Use Timbersaw (Dota2)

• Timber Chain should be maxed out first because of its low cooldown, increased range, and guaranteed pure damage.
  • When chasing, he can use it to catch up to heroes, especially against those who have quick escape abilities.
  • When running away, he can also use this to escape. Make sure to use the jungle as an escape path, since it contains numerous trees for you to use.

• If you are ready to gank in a side lane and are behind trees, use your Chakram to destroy the trees in front of you, then use your Timber Chain on the other side of the lane; after this, a well placed Whirling Death can almost ensure a kill in many situations.

• For Timbersaw, tankiness and mana regeneration are a must: items like Bloodstone and Shiva's Guard really help him in many ways. Other interesting items may be Vanguard, Scythe of Vyse, Hood of Defiance, Heart of Tarrasque or Eul's Scepter of Divinity, but they don't give both tankiness and mana regeneration.

• If your team doesn't have an initiator, try initiating with Chakram, followed by Timber Chain and Whirling Death. Items like Pipe of Insight, Blade Mail and Shiva's Guard can aid you in initiating.

• One of Timbersaw's weaknesses is his lack of disrupting spells; he suffers against heroes who excel at channeling spells to harm their opponents. In this case, equip him with an item that has a quick disable, such as Eul's Scepter of Divinity.

• When a hero is escaping through only one potential exit, use Chakram to block that path; if successful, the enemy hero will be forced to run through the blade, losing health immensely and slowing down in the process. To further slow the hero down, cast Whirling Death while the hero is in the middle of the Chakram, making sure that you don't widen the enemy hero's escape path.

• When deployed, Chakram's movement is somewhat delayed; make sure to predict your target's path and cast it ahead of time.

• Chakram synergizes well with multi-target skills that disable free movement, such as Enigma's Black Hole, Treant Protector's Overgrowth, or even Disruptor's Kinetic Field.

• Aside for tanking damage in team fights, Reactive Armor can also be used as a quick health regeneration boost. You can either visit the easy creep camps since they do small damage and come in groups, or tank lane creeps when no enemy hero is present. As long as there are multiple targets attacking you in quick succession, the skill will stack sooner, and you will be able to heal faster. Make sure you're receiving damage that is lesser than what you are able to regenerate.

• Aside for escaping, Timbersaw's skill set also makes for good chasing. Cut down trees that get in your way to widen your path and even prevent juking.

• The trees summoned by Nature's Prophet through Sprout are still standard trees to Timbersaw. As an enemy, you can easily cut it down to escape, or free allies who are trapped within it. As an ally, this can be used to your advantage when escaping (as Prophet can summon trees in a convenient location for you to use Timber Chain) or when fighting (Prophet can summon trees closer to you when no other tree is present, so that you can deal pure damage when casting Whirling Death). 

source:  http://dota2.gamepedia.com/Timbersaw