Thankfully, I'm not employed by VIA to answer these questions. You know a lot more than I do - it's why I always like reading your posts on this thread.
I'd be much more interested in getting your unique insights outright rather than having you beat me over the head with them after answering your unnecessarily snide rhetorical questions.
My genuine intent was to show you the limitations in your envisioned solutions, but I have to concede that I might have also perceived them as “unnecessarily snide rhetorical questions” if they had been directed at me, so my sincere apologies for carelessly giving you this impression! I remember very well when I was starting my presence in this forum a half-decade ago and how happy I would have been if one of the participants in these discussions would have identified as a VIA employee...
You are of course right that unlike you I actually get paid for finding answers to the questions I’ve raised and that it would therefore be unreasonable to expect you to find answers yourself. I will therefore try to provide an answer to the two questions you’ve raised, which will be as elaborate as is possible (while watching my four month old peacefully sleep in this Hotel’s breakfast room and while my wife gets some well-deserved extra sleep):
Concerning the viability of night trains between Toronto and Chicago, I would like to refer you to an excellent
report conducted by Steer, Davis and Glee for the European Parliament, which has studied extensively the various factors which contribute to the decline of night trains observed in Europe and beyond:
As you can see in this table (to be found on page 48 in the report I linked above), night trains are at a significant cost disadvantages compared to other (i.e. day) trains or modes (esp. the airplane) and most of these disadvantages also apply to North America. This doesn’t stop the Canadian from obtaining a cost-recovery rate which is only a few percentage points below the corresponding figure on the Corridor, but we are talking more about a land cruise which serves as a “destination in itself” to mostly foreign tourists than as the intercity night train for business and more traditional leisure travellers, which you envision for Toronto-Chicago...
Concerning the practicality of border checks on the Toronto-Detroit-Chicago corridor, you seem to be inspired by how the Eurostar works between London and Paris or Brussels: However, the Eurostar does no longer transport domestic passengers (at least not prior to the border crossing), which is no problem given that London-Ashford and Brussels-Lille-Paris are more than sufficiently served by domestic high-speed trains (note that most continental European countries like France, Belgium or the Netherlands form an internal market which reduces border complexities to that of crossing provincial/territorial/state borders within Canada and the United States). Lille-Brussels used to be served by Eurostar services, but this Remains only possible in the westbound direction ever since the UK has moved its border checks onto the European mainland and this is also the reason why trains inbound to London from Eurostar destinations without pre-clearance facilities (e.g. Rotterdam, Amsterdam or Marseilles) have to stop at either Brussels or Lille so that all passengers can leave the train and re-enter through the pre-clearance facility. Such an arrangement would of course be also possible at the Canadian-US border, but my experiences on board the Adirondack and from tracking the on-time performance of the Maple Leaf suggest that this would delay the journey by significantly more than the 15 minutes it adds to the journey on the Eurostar.
With pre-clearance facilities being unlikely to ever getting built in Toronto (lack of space), Oakville/Aldershot/Brantford/London/Chatham/Ann Arbour/Michigan City (lack of passenger potential to justify building and staffing such a facility) or Chicago (lack of both), this only leaves the Vancouver model, which would be to build a pre-clearance facility in Detroit and to let all international trains terminate here. Whereas Detroit’s current Amtrak station would be too small for such facilities,
Ford’s plans to redevelop Michigan Central station into an urban mobility hub could be a god-sent: There are no current (St-Lambert/QC, Oakville, Aldershot, Grimsby, St-Catherines or Niagara Falls/ON) or potential (Surrey/BC or Hamilton) intermediary stops which would be foregone if all border checks were centralized in Detroit and the “transiting” distance between the tunnel and Michigan Centrale station is even shorter than in Rousses Point (and a small fraction of that into Vancouver).
In short, I don’t see any business case for offering a night train between Toronto and Chicago (because of the usual challenges of offering intercity night train services plus the border challenges, which would likely result in border checks having to be performed in the dead of the night), but I do see a potential to extend the Toronto-Windsor services into Detroit (with a pre-clearance facility at a revitalized Michigan Central station) with attractive connections towards Chicago. Having to move the train station in Windsor is certainly not a showstopper...
Cant be because this service is provided by a foreign entity. Wheres our train down to Detroit?
I don’t understand the problem you are highlighting: The Adirondack and the Cascades are Amtrak services operating into Canada and the Maple Leaf is an Amtrak train operated with VIA Rail crews on this side of the border (while the Atlantic was a VIA train transiting through the United States), so what would be the regulatory problem with operating an international service like Toronto-Windsor-Detroit(-Chicago)?