I actually think the high price is just for the launch as people buying hardware at launch/non holiday period are either hardcore Nintendo fans or have plenty of capital that $299 ain't all that much and it's sounding like supply will be limited at launch making people happy to drop the $299 then the more casual and people buying it for gifts arrive later.
I think the first bundle could be a $299 Splatoon 2 bundle and will arrive in Summer which will offer better value and by holiday 2017 there will definitely be $299 bundles avaliable.
They will want to make things really competitive price they could be waiting for holiday 2017 to launch a $199 handheld only version (no dock or joycon grip) as looking at these prices individually for these $199 seems reasonable and will open up to big sales from parents grabbing it for Christmas. 2017 might be to early but I'm sure by holiday 2018 this will happen as there is an audience who just want it as an handheld.
Edit: In USD as it's just easier even though OP costs were in CAD :)