so i recently fired up oblivion again for the first time in over a year and while creating my character i was struck with an interesting idea. after realizing my character looked almost identical to my current character in skyrim i decided he would be the dragonborn's great-great-great grandfather.

so heres what im doing, both of the characters have an almost identical skill set (conviently my skyrim characters skills lined up with the "scout" class in oblivion) they both use similar equipment and have the similar morals. i jump back and forth between the two characters as my mood strikes me but im trying to do it in a way that makes sense with both of the main quests. while playing oblivion i view my character's actions as though they are a dream or a vision of my skyrim character.

this is allowing me to explore aspects of skyrim that i hadn't had any interest in exploring before, specifically the imperial side of the civil war and the blades faction quests and it is also breathing new life into oblivion(prior to this playthrough i had only played oblivion very casually)

does anyone else have any similar playthroughs or characters? or have any tips on ways to further integrate my two characters?

Ive never done that before but its definately an interesting idea.

You deserve a high five through the space time continuum.

The closest I've done is tie backstories of characters together. For example, my Oblivion character Khulain is a vampire who, 200 years after the Oblivion Crisis, kidnapped my Skyrim character. My Skyrim character, Thadious, escaped captivity and fled to Skyrim but picked up many of Khulain's dark arts during the time he spent captured.

I also made an Oblivion character, Marr'Taan, who was a younger brother to my Morrowind character, Aalaan.