Join Date: Oct 2005
Location: Southwestern Ontario
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Leaving aside questions of cost/difficulty, there's another factor to think through before going ahead: your bike's geometry.
The Trek DS series bikes are, quite rightly, designed around (some form of) 'flat bars'. Most importantly, effective top tube length. Take a Medium (17.5) DS: it has an effective t/t length of 608 mm. which is long even by 'flat bar bike' standards. A typical 'Medium' road bike (drop bars) will have an effective t/t of around 550 mm (+/- 5 mm or so).
If you install drops on your bike, even short-reach bars with a short stem, you are going to be reeeeally stretched out. This might possibly 'work' for you, but I'd be surprised if it did. Just something to think through before going ahead.