i like my cross check. it's awesome. that said, i'm not sure how awesome it would be from manhattan to long island, it's more for light touring, and i use it as a commuter from BK to manhattan and would use it for long rides too (30 mi). and the pothole situation is out of control. thicker tires would help you with that but add some rolling resistance. i think it would be worth it for 700 x 28-35mm tires.

i also would think a serious touring bike would suit your needs better, but i don't have so i don't really know. so yeah, it depends on what you really want. good luck finding something!

also i have had a road bike in the past and it suited my needs perfectly. and for fenders? SKS raceblades. i had them on both the road bike and have them now on my current commuter and i don't have the wet problems i had before, they keep my relatively dry, just some random mud splats around my calves and ankles, not too much. and they weigh hardly anything.