Fastest/easiest way to re-enter US in NYC on a TN visa
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It's certainly allowed to leave the US and re-enter in another status; using the land border or an airport won't change that. Another itinerary to consider is flying to an airport near the Canadian border and then crossing by land to Canada and back. You might find less expensive tickets.
It's not legal to work in the US if you enter as a tourist, however, so you cannot start your job until you've left and re-entered.
(There's another option aside from leaving and re-entering the US, which is applying for an in-country change of nonimmigrant status, but that costs $370 and takes a long time, so going to Canada and back is definitely better.)
One small consideration is preclearance; if you want to actually enter in NYC (that is, have your TN documents evaluated by an officer in New York), you'll have to fly somewhere other than Toronto or Montreal (or any other major Canadian airport).
If you rent a car and drive over the border and back, consider the (probably very small) risk of being refused entry. If that happened, you might be unable to return the car on time.
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