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@jastel we did this trip and a trip report can be found Here. We caught the ferry between Seattle and Victoria, it is and easy journey as it leaves from and arrives in town. We booked the the upstairs front section which was quite nice but if I was to do it again I would head downstairs and to the back of the ferry before it docks. The top front section is the last to disembark so you get caught being almost last to clear customs. We used the sea plane service between Victoria and Vancouver depending on the fare class you book you can get anywhere between a few pounds of luggage to guaranteed 50Lb with an additional 50Lb as standby. As we were not flying out until late afternoon we just dropped our luggage off after check out and they moved it across during the day and it was waiting for use on the Vancouver side and from memory they charged us a $10 storage fee. The sea plane terminal if walking from most hotels and was easy to get to. The chopper service was slightly more expensive and luggage was capped at 50Lb, helipads on the Victoria side are not that close to town and if you have luggage I would recommend vehicle transport. The helipad is about a 30 minute walk from town.
As for the trains we caught the train between Toronto and Montreal, it was all very easy and civilised. In Toronto our accomodation was about 3 blocks from the station so an easy walk with luggage. At the Montreal end we just transferred to the local line and caught a local train to the closest station to our accomodation. We were not able to catch the train between Montreal and NYC as the Adirondack Line had not recommenced operating. The Maple Leaf Line (Toronto to NYC) had recommenced however we were after the Adirondack Line due to the time of the year and the route. We ending flying YUL-LGA, if you also use *A AC is the better option as CA is the only lounge available in the terminal (CA/US routes) which is also used by AA. I have been to CA a few times but do not consider myself an expert, YVR I tend to walk however the trains I have used are not complicated, in Toronto mainly use the bus system, Montreal only has a 4-5 lines that are all colour coded and exchange stations are easily identifiable. @RooFlyer may have some more suggestions.
I have seen it 10 years ago but now it has a Space Shuttle it might get another visit.