Where do I fit into this equation? I use a road bike, clean with no rack & fenders and aggressive setup, race-fit jerseys but like as not running shorts and tennis shoes. It feels more like "roady" than commuter although better than 90% of the time I'm out it's commuting.
There is one "hill" just before the Greenway on which I'll always try to pass anyone I see. It's all of 45 feet vertical but it's the only rise on the greenway route so it's my daily "interval training" (I like to break my intervals up, one per day). So I generally swoosh by the cargo bikes and commuters and the occasional roadies who are resting up from the Windward hills. Unfortunately I can count on one finger the matches I have in reserve and that effort burns one of them, so the latter roadies often catch me less than a mile into the Greenway.