If you are doing one tool path i.e. Male, like you lighting post, and still having problems finishing a part before moving to the next. You have to make sure that your show fill works, if it doesn't make path. If you are doing two tool paths or more then you have to select all the male pieces, make path, then select all online pieces and make path as well. Create individual tool paths for each then sequence as Matt posted before then select the whole part and group the object. After this is completed you can do an array to make as many parts as needed.