First Halo: Reach, then Halo 3, and more recently Halo 3: ODST - Legendary each one. Once I did Reach I felt compelled to do the others on Legendary. I had already done all 3 on Heroic. I rarely resist a video game challenge. As the Rookie, I already had access to all the caches and some Mongoose bikes. Still getting around was a haphazard in trying to avoid fights whenever possible. As for the mission flash backs, I took it slow and tried to pick them off since well as the Rookie - I got no shields or any armor abilities. It took fewer days to finish to ODST than it took to finish 3.
Still like all other Legendary play through I did one level at a time save for Data Hive and Highway.