US employer suggests two 90 day contract periods instead of work visa. Is this okay? [closed]

Your employer is full of it and sounds dodgy as hell. Canadians do not need a US visa to visit or study in the US, but they most certainly need one for any sort of work, including unpaid internships.

Now of course you could lie and say you're visiting the US for some other reason, but like the embassy link above says:

All Canadians are reminded that U.S. law requires all foreigners to qualify for the desired stay and purpose at the time of their initial entry. A visitor who intends to live, work or study in the U.S. without disclosing this information beforehand may be permanently barred from the U.S.

I'm also a bit surprised they're talking about applying for an H-1B. Is there some reason you don't qualify for a TN-1, J-1 or H-3, which are all much easier to get?

To answer the original question, you would be working illegally. Period. Full stop. Do not pass "Go" and do not return to the USA for 5 years. Go to Detroit from Windsor ( walking distance ) play in a club, get your hotel room and bar bill covered -> also working illegally.

Your employer will also come to the attention of INS (and possibly homeland security), so it's just a bad idea for everyone involved.

To answer the other question, a journalist, trainer, technician etc. may be doing work while in the other country, but if they are directly employed in their home country it is not considered local work. So a reporter for the Windsor Star could cover the club performance, arrest and deportation back across the bridge because they are still working for a Canadian company. This happens all over the world - most countries allow this kind of work on a visitor visa as it does not impact the local job market (but would severely impact international trade if you needed a work visa to go to a meeting).