Apparently OP didn't try this, but I just wanted to add that my vote would be "no". Unless there were multiple backup options, I would even hesitate to book a 2 hour D->I connection in NYC in the afternoon/evening even if it was all at JFK. NYC is the most congested airspace in the country, flights into LGA/JFK are routinely delayed in the afternoons even with good weather, and a single thunderstorm would surely wipe out the entire buffer. Adding the transfer from LGA to JFK eats up 45 minutes if everything runs perfectly, so you're really talking about a 1:15 connection in perfect conditions.