At some level, DotA is still a strategy game and requires some amount of strategic thinking. More than "I can do X against Y," you must think "I can do either A or B, but not both."
Where are you going to ward? You cannot ward everywhere. How are you going to spend your gold? You cannot buy everything. Are you going to split push or defend? You cannot be in both places.
We thus require a deeper understanding of our heroes, and a deeper understanding of the game and the state of affairs.
These days when I play Gyrocopter (and I rarely play him these days), I am loath to make Drums. This hero has no movement speed issues, no shortage of mana, and attack speed is a minor consideration. I stop at the bracer: the opportunity cost of finishing drums is too high for the benefit.
I've recently been playing Chen, and this hero is presented with several strategic choices. First, every item you buy delays your Mekansm. Is Arcane boots worth going first? No. What about wards so your other support isn't dirt poor? It's harder to say.
Do you spend time trying to gank, which will delay your own development? Do you help your safe-lane defend an aggressive tri-lane or do you 2-2-1 offensively?
When you have engaged in a skirmish and are left weak, do you go back to the well or crow yourself regen? Here we arrive at a deviation. Compared with other supports, your opportunity cost of running back to the well to heal is too high. You can continue to gain levels and gold in the jungle. Bring yourself some pots and clarities