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Where will you commute to on Long Island? Unless you're willing to spend at least 2 hours commuting each way, I wouldn't commute to Long Island. First, you'd have to take Metro-North to Grand Central Station (monthly pass from Stamford around $275, significantly more from New Haven). Then, you'd need to go from Grand Central to Penn Station probably via subway. There are no direct subway routes between the two stations. You'd have to transfer and walk a few blocks. Then, you'd take the Long Island Railroad.
The commute from Stamford to Grand Central is 45 minutes. The commute from New Haven is about 100 - 110 minutes. The subways are unpredictable so you may miss your train to go to Long Island. I'm not sure how often the trains run since most people on LI commute into Manhattan, not out of it.
I think it would be a very long and expensive commute.
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