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08/29/23 Good afternoon, poseidon72.  Chances are that he'd be denied entry if he were detected trying to enter on his second passport after reaching the limit on his primary one, but I'm not at all sure that he would be detected, so chances of getting in are probably pretty good.

Once he passes the 180 day mark he'll start running afoul of other laws, e.g, tax liability,  driving on a foreign license,  etc., so keeping a low profile with respect to the authorities will become a better and better idea.

Becoming a permanent resident is the polar opposite of "keeping a low profile  with respect to the authorities", so if that's part of his plans for romantic or other legal reasons, he should start the process early in an unquestionably legal visit on the passport of his primary country of residence, to keep things as simple as possible.

@abthree Thank you, yes he would never pass the 180 mark on his original Canadian passport, so it would be within his allowable limit with each passport.

08/29/23 @abthree Thank you, yes he would never pass the 180 mark on his original Canadian passport, so it would be within his allowable limit with each passport.
-@poseidon72

I should have made myself more clear.  When he's been in the country 183 days he starts hitting those tripwires because he's still the same foreigner, regardless of the color of his passport.

They'll have his data matched in the computer system regardless of the passport used.

He'll get caught, maybe questioned, I don't know about what sanctions he may or may not get, so, it's not something I can answer.

@poseidon72  Hi! I have dual citizenship Brasil-USA.  Whenever I go to Brazil and come back. I always present both passports. In the USA, they only care about the USA passport (you always enter the citizen's line at immigration). In Brazil, they look both. There was one time that I only presented the USA passport and they asked for the Brazilian and said I had to present both.  I have a friend whose Brazil~s passport expired and she got in and out of Brazil with her Norwegian passport. Immigration in Brazil did not like it and she said to call (at the time of the event) the Norwegian embassy because she was a citizen and had the right to go and come back since once she had a Brazil~s visa permit on her Norwegian passport. They stopped bugging her.