So I've been thinking of exploring every cave,ruins,forts settlements and anything else thats explorable in the Shivering Isles does anyone have any tips for me on how to keep myself from losing interest with this goal of mine

Look for the five skulls of the Hill of Suicides Do so, and you get a greater power reanimation spell for 60 seconds.

Look for a special Easter Egg in the northern part of the Isle.
Help a knight down on his luck.
Help some friendly ghosts.... no, not Casper.
Discover the sad tale of a woman in a cave.
Look for Amber and Madness matrices.
Find the coolest dungeon ever, in Mania.