Geographic location of the bug: arrived on boat, Caribbean somewhere between Trinidad and Martinique, think it flew on board
Time: 11:09 AM EDT
Your letter to the bugman: Looks like a Jeruselem Cricket but has wings.
How you want your letter signed: Chris
This is a wonderful image of a Mole Cricket, a primarily subterranean dweller that is found in many parts of the world. Some species are capable of flight. We have even had folks claim they can swim.