Should we have just gone ahead and annexed Canada back in the 1790s ?
You tried that in 1812.
And in 1813.
And in 1814.
Then you gave up.
We should have given it a second try when Britain balked at paying back
its WWI debts: https://en.wikipedia.org/wiki/War_Plan_Red
https://www.youtube.com/results?search_query=war+plan+red+documentary
It probably would've ended in a stalemate considering how large the Royal
Navy was back then compared to ours...
There's a 100-year old joke about dealing with the Canadian military ... at
the end of WW I, various allied troops were shipped to camps on Salisbury
Plain in England, to await transport home:
Sentry at Salisbury Plain Camp: Halt! Who goes there!
Soldier: Privates Adams and Johnson, Australian Army.
Sentry: Pass, Australians.
Sentry: Halt! Who goes there!
Soldier: Corporal Smit, South African Army.
Sentry: Pass, South African.
Sentry: Halt. Who goes there!
Soldier: Mind your own f***** business, you bloody moron!
Sentry: Pass, Canadian.