Not naive at all, and I wondered myself if this might be the plan. Because ML.
In theory that’s possible, yes, but it is highly undesirable because a) leaves no flexibility if the other tracks is out of service for some reason and b) there’s always the chance that a train might have to back up and c) it does push the train’s braking effectiveness to the limit, with possible wheel skids when braking hard. That damages the wheels.
Triangle calculator gives 729 feet and 2 degree slope gives you 25 feet vertical elevation.
That's enough for a truss rail overpass with room for OCS underneath. GO electrification minimum clearance is 5946mm (19.5 feet) if you custom build it with the right materials, plate, etc.
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source)
25feet can be doable with 19.5 feet clearance + 5.5 feet rail deck underneath trussed bridge or (set of) bucket decks.
Tolerances are tight but should be doable without violating Metrolinx slope specs, and I've seen railroad truss bridges thinner than 5.5 feet from bottom-to-rails by using a slim railroad deck and a truss to stiffen a thin rail deck bridge. If you've driven east of Toronto on 401 through Pickering, you will often see this weird combination of 3 different rail bridge deck thicknesses:
-- Traditional I-deck at left
-- Truss bridge in middle
-- Bucket deck at right
(source --
http://beachburg.blogspot.com/2015/01/railway-bridges-of-ontario.html )
Theoretically, how frequently will a train need to do braking in that section? GO trains do have particularly effective brakes as we already know how it just decelerates nicely to a stop from 70-80kph to 0kph in the mere length of a platform, and doing so reliably without creating flat spots on the wheels.
As you can see, 729 feet with 2 degrees or (less) is no problem keeping within Metrolinx specs.
You just need to
build a thin railroad deck and call it a day, and then you've got plenty of underpass room for OCS-height capable of supporting locomotive Bombardier BiLevels in both directions.
The good news is that you only need to build an underpass for a single track -- not a giant 4 track corridor -- a very short air hop. So should be easy to keep the rail deck thin, even just simple I-beams. But you could also try to decrease the slope to ~1.8 degrees, and use an even thinner bridge; or use it to zero the gradient at the curve before the 729 feet. The tricky part is building the bridge without distrupting service...