I don't mean full Jared Diamond or anything, but something more like a comparison about what similarities there were between island nations like England, Japan, Indonesia, etc. or those that lived in more arid climates or highlands or what have you. In what ways did these geographical features influence these peoples and are there any noticeable similarities between their cultures, politics, and social structures?
No. With the level of specificity you've given, it's doubtful that there any generalizations that one could actually make, and any one could make would be so broad as to be useless.
The real issue underlying this is that their insularity pales in importance next to other factors: climate, the availability of resources, varying relationships to neighboring people, different cultural histories and so on. The most you could say is that both Britain and Japan are islands, and sometimes that affects their histories, but not in any consistent or predictable way. The same goes for Madagascar, or Cuba, or Sicily, or Greenland, or New Zealand, or Java, etc. etc. Or, as I opened with, any generalization you could make about island life would be so broad as to be useless.