I would definately hand quilt it, it at all possible. It is much easier to control puckers and such, and easier to maneuver to avoid the kind of problems you are afraid of running in to. You have to quilt round the outline the sailboat to make it pop out. You can do it. Just take your time and everything will be great. Would be nice though if you could post a pic, to make it easier to help you with your issues.