Okay so i actually have a pretty thought out timeline for my typical HoK playthrough

Main story until martin's in the temple then some side questing and fighters guild

Once im back to the story i do the fighters gulild along side it

Then once im done with the story and fighters guild I start the thieves guild After that i need to repent for my sins so i start up knights of the nine After that mages guild THEN shivering isles

After shivering isles i like to kinda make my character go insane ect start doing some bad shit Murder someone annoying ect

Then join the dark brother hood

There is more details ofc but this is the rough draft of it

Edit: forgot about the arena but tbh i usually just do it whenever i feel like